Product Name

  • Name

    Vitamin K2(35)

  • EINECS
  • CAS No. 2124-57-4
  • Article Data11
  • CAS DataBase
  • Density 0.961 g/cm3
  • Solubility
  • Melting Point 54 °C
  • Formula C46H64O2
  • Boiling Point 720.1 °C at 760mmHg
  • Molecular Weight 649.013
  • Flash Point 254.9 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 2124-57-4 (Vitamin K2(35))
  • Hazard Symbols
  • Synonyms 1,4-Naphthalenedione,2-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)-3-methyl-,(all-E)-;1,4-Naphthalenedione,2-[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl]-3-methyl-(9CI);1,4-Naphthoquinone,2-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)-3-methyl-,(all-E)- (8CI);MK7;Menaquinone 7;Menaquinone K7;Vitamin MK7;1,4-Naphthalenedione,2-[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-yl]-3-methyl-;
  • PSA 34.14000
  • LogP 14.09740

Synthetic route

2-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-1,4-dimethoxy-3-methylnaphthalene
1218784-62-3

2-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-1,4-dimethoxy-3-methylnaphthalene

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 4.08333h;80%
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 4.08333h;80%
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 0.75h;72%
With ammonium cerium (IV) nitrate In dichloromethane; water; acetonitrile at 0℃; for 0.75h;0.753 g
C50H74O2
1597486-88-8

C50H74O2

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In dichloromethane; water; acetonitrile at 0℃; for 0.25h;72%
2-(chloromethyl)-3-methylnaphthalene-1,4-dione
31599-79-8

2-(chloromethyl)-3-methylnaphthalene-1,4-dione

C33H52

C33H52

trimethylaluminum
75-24-1

trimethylaluminum

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Stage #1: C33H52; trimethylaluminum With zirconocene dichloride In toluene at 0℃; for 1h;
Stage #2: 2-(chloromethyl)-3-methylnaphthalene-1,4-dione With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h;
65%
(2E,6E)-farnesyl acetate
4128-17-0

(2E,6E)-farnesyl acetate

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C
2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C
3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
5.2: -78 - 20 °C
6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
9.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
9.2: 4.5 h / 0 °C / Inert atmosphere
10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C
2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C
3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
5.2: -78 - 20 °C
6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
10.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
10.2: 5 h / 0 °C / Inert atmosphere
11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane / 14 h / 0 °C
1.2: 2 h
2.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.75 h / -45 - -40 °C
2.2: 2 h / 0 °C
3.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: sodium methylate / methanol / 4 h / 0 °C
5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
7.1: triphenylphosphine; bromine / dichloromethane / 0 °C
8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
8.2: 12 h / Inert atmosphere
9.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
10.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
11.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
E,E,E-12-hydroxyfarnesyl acetate
93787-91-8

E,E,E-12-hydroxyfarnesyl acetate

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
3.2: -78 - 20 °C
4.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
5.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
7.2: 4.5 h / 0 °C / Inert atmosphere
8.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
3.2: -78 - 20 °C
4.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
6.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
7.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
8.2: 5 h / 0 °C / Inert atmosphere
9.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.75 h / -45 - -40 °C
1.2: 2 h / 0 °C
2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: sodium methylate / methanol / 4 h / 0 °C
4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
6.1: triphenylphosphine; bromine / dichloromethane / 0 °C
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
7.2: 12 h / Inert atmosphere
8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
(2E,6E,10E)-3,7,11-trimethyl-12-(phenylsulfonyl)-dodeca-2,6,10-trien-1-yl acetate
1597486-72-0

(2E,6E,10E)-3,7,11-trimethyl-12-(phenylsulfonyl)-dodeca-2,6,10-trien-1-yl acetate

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
5.2: 4.5 h / 0 °C / Inert atmosphere
6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
6.2: 5 h / 0 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12
3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12
3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
5.2: 4.5 h / 0 °C / Inert atmosphere
6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
6.2: 5 h / 0 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 °C
2.2: -78 - 0 °C
3.1: sodium methylate / methanol / 2 h / 20 °C / pH 12
4.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
7.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C
1.2: -78 - 20 °C
2.1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12
3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: pyridine / N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 °C
2.2: 5 h / -78 °C
3.1: sodium methylate; methanol / 2 h / 20 °C
4.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
5.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
7.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
8.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
C38H56O4S
1597487-01-8

C38H56O4S

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
2.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
4.2: 4.5 h / 0 °C / Inert atmosphere
5.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
5.2: 5 h / 0 °C / Inert atmosphere
6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12
2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12
2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
6: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-12-(phenylsulfonyl)tetracosa-2,6,10,14,18,22-hexaen-1-ol
1597486-78-6

(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-12-(phenylsulfonyl)tetracosa-2,6,10,14,18,22-hexaen-1-ol

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
3.2: 4.5 h / 0 °C / Inert atmosphere
4.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
2.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
4.2: 5 h / 0 °C / Inert atmosphere
5.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
4: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
4: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
5: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
(2E,6E,10E)-12-bromo-3,7,11-trimethyl-2,6,10-dodecatrienyl acetate
104423-44-1

(2E,6E,10E)-12-bromo-3,7,11-trimethyl-2,6,10-dodecatrienyl acetate

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
2.2: -78 - 20 °C
3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
6.2: 4.5 h / 0 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
2.2: -78 - 20 °C
3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
5.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
7.2: 5 h / 0 °C / Inert atmosphere
8.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: sodium methylate / methanol / 4 h / 0 °C
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: triphenylphosphine; bromine / dichloromethane / 0 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / Inert atmosphere
7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol
68778-93-8

(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
3.2: 5 h / 0 °C / Inert atmosphere
4.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: triphenylphosphine; bromine / dichloromethane / 0 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 12 h / Inert atmosphere
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: triphenylphosphine; bromine / dichloromethane / 0 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 12 h / Inert atmosphere
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
4: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
1-bromo-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
74610-00-7

1-bromo-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
2.2: 5 h / 0 °C / Inert atmosphere
3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere
2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere
2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
4.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
phenylsulfonyl hexaprenyl bromide
1597486-86-6

phenylsulfonyl hexaprenyl bromide

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
2.2: 4.5 h / 0 °C / Inert atmosphere
3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
C62H82O6S2
1597486-87-7

C62H82O6S2

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
1.2: 4.5 h / 0 °C / Inert atmosphere
2.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
C56H78O4S
1597486-91-3

C56H78O4S

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
1.2: 5 h / 0 °C / Inert atmosphere
2.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
(2E,6E,10E)-3,7,11-trimethyl-12-oxododeca-2,6,10-trien-1-yl acetate
40266-21-5

(2E,6E,10E)-3,7,11-trimethyl-12-oxododeca-2,6,10-trien-1-yl acetate

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C
2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
4.2: -78 - 20 °C
5.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
9.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
9.2: 5 h / 0 °C / Inert atmosphere
10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C
2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
4.2: -78 - 20 °C
5.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
6.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
7.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
8.2: 4.5 h / 0 °C / Inert atmosphere
9.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.5 h / -10 °C
2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C
4.2: -78 - 20 °C
5.1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12
6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
7.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
8.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
9.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
1,4-diethoxy-2-methyl-3-[(2E)-3-methyl-4-(phenylsulfonyl)-2-buten-1-yl]naphtalene
1597486-65-1

1,4-diethoxy-2-methyl-3-[(2E)-3-methyl-4-(phenylsulfonyl)-2-buten-1-yl]naphtalene

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
2.2: 4.5 h / 0 °C / Inert atmosphere
3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
2.2: 5 h / 0 °C / Inert atmosphere
3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Farnesol
106-28-5

Farnesol

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere
2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C
3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C
4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
5.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
6.2: -78 - 20 °C
7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
10.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
10.2: 4.5 h / 0 °C / Inert atmosphere
11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 12 steps
1.1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere
2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C
3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C
4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
5.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness
6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
6.2: -78 - 20 °C
7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
9.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
10.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice
11.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice
11.2: 5 h / 0 °C / Inert atmosphere
12.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C
2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C
2.2: -78 - 20 °C
3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12
4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice
5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice
6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere
6.2: 4.5 h / 0 °C / Inert atmosphere
7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C
View Scheme
1,4-dimethoxy-2-methylnaphthalene
53772-19-3

1,4-dimethoxy-2-methylnaphthalene

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
2.2: 2.25 h / 0 °C
2.3: 0.67 h / Reflux
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3.2: 14 h / Inert atmosphere
4.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
6.1: iodine / chloroform / 6 h / 20 °C
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
7.2: 12 h / Inert atmosphere
8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
2.2: 2.25 h / 0 °C
2.3: 0.67 h / Reflux
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3.2: 14 h / Inert atmosphere
4.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
6.1: iodine / chloroform / 6 h / 20 °C
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
7.2: 12 h / Inert atmosphere
8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
10.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tin(IV) chloride / 1,2-dichloro-ethane / 20 - 80 °C
2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: tin(IV) chloride / 1,2-dichloro-ethane / 5 h / 80 °C
2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
4: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
1,4-dimethoxynaphthalene-3-methyl-2-carboxaldehyde
17827-40-6

1,4-dimethoxynaphthalene-3-methyl-2-carboxaldehyde

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
1.2: 2.25 h / 0 °C
1.3: 0.67 h / Reflux
2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 14 h / Inert atmosphere
3.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
5.1: iodine / chloroform / 6 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / Inert atmosphere
7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
1.2: 2.25 h / 0 °C
1.3: 0.67 h / Reflux
2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 14 h / Inert atmosphere
3.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
5.1: iodine / chloroform / 6 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / Inert atmosphere
7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
9.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
(1,4-dimethoxy-3-methylnaphthalen-2-yl)acetaldehyde
51794-08-2

(1,4-dimethoxy-3-methylnaphthalen-2-yl)acetaldehyde

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 14 h / Inert atmosphere
2.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
4.1: iodine / chloroform / 6 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 12 h / Inert atmosphere
6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 14 h / Inert atmosphere
2.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
4.1: iodine / chloroform / 6 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 12 h / Inert atmosphere
6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
8.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-enoic acid ethyl ester

4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-enoic acid ethyl ester

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
3.1: iodine / chloroform / 6 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 12 h / Inert atmosphere
5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
3.1: iodine / chloroform / 6 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 12 h / Inert atmosphere
5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
7.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
2-[3-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-1-methylpropenyl][1,3]dithiane

2-[3-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-1-methylpropenyl][1,3]dithiane

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere
2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere
2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
4.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
(E)-4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-en-1-ol
94828-29-2

(E)-4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-en-1-ol

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.1: iodine / chloroform / 6 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 12 h / Inert atmosphere
4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.1: iodine / chloroform / 6 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 12 h / Inert atmosphere
4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
6.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-enal
99306-85-1

4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-enal

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: iodine / chloroform / 6 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 12 h / Inert atmosphere
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: iodine / chloroform / 6 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 12 h / Inert atmosphere
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
2-(2,6,10-trimethylundeca-1,5,9-trienyl)[1,3]dithiane

2-(2,6,10-trimethylundeca-1,5,9-trienyl)[1,3]dithiane

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: sodium methylate / methanol / 4 h / 0 °C
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: triphenylphosphine; bromine / dichloromethane / 0 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / Inert atmosphere
7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
2.1: sodium methylate / methanol / 4 h / 0 °C
3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
5.1: triphenylphosphine; bromine / dichloromethane / 0 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / Inert atmosphere
7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
9.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
menadione
58-27-5

menadione

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: water; sodium dithionite / ethyl acetate; water / Inert atmosphere
2.1: potassium carbonate / acetone / 6 h / Reflux
3.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
4.2: 2.25 h / 0 °C
4.3: 0.67 h / Reflux
5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 14 h / Inert atmosphere
6.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
8.1: iodine / chloroform / 6 h / 20 °C
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
9.2: 12 h / Inert atmosphere
10.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
11.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
12.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: water; sodium dithionite / ethyl acetate / Inert atmosphere
2.1: potassium carbonate / acetone / 6 h / Reflux
3.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
4.2: 2.25 h / 0 °C
4.3: 0.67 h / Reflux
5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 14 h / Inert atmosphere
6.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere
7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
8.1: iodine / chloroform / 6 h / 20 °C
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
9.2: 12 h / Inert atmosphere
10.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
11.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
12.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: sodium dithionite / ethyl acetate; water / 0.33 h / 20 °C / Inert atmosphere
2: potassium carbonate / acetone / 6 h / Reflux
3: tin(IV) chloride / 1,2-dichloro-ethane / 20 - 80 °C
4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C
5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: sodium dithionite / ethyl acetate; water / 0.33 h / 20 °C / Inert atmosphere
2: potassium carbonate / acetone / 6 h / Reflux
3: tin(IV) chloride / 1,2-dichloro-ethane / 5 h / 80 °C
4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C
5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
6: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C
View Scheme
Farnesal
502-67-0

Farnesal

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: iodine / chloroform / 6 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: sodium methylate / methanol / 4 h / 0 °C
4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
6.1: triphenylphosphine; bromine / dichloromethane / 0 °C
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
7.2: 12 h / Inert atmosphere
8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: iodine / chloroform / 6 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
3.1: sodium methylate / methanol / 4 h / 0 °C
4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
6.1: triphenylphosphine; bromine / dichloromethane / 0 °C
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
7.2: 12 h / Inert atmosphere
8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
10.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
acetic acid 3,7,11-trimethyl-12-[2-(2,6,10-trimethylundeca-1,5,9-trienyl)[1,3]dithian-2-yl]-dodeca-2,6,10-trienyl ester

acetic acid 3,7,11-trimethyl-12-[2-(2,6,10-trimethylundeca-1,5,9-trienyl)[1,3]dithian-2-yl]-dodeca-2,6,10-trienyl ester

menaquinone-7
2124-57-4

menaquinone-7

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium methylate / methanol / 4 h / 0 °C
2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
4.1: triphenylphosphine; bromine / dichloromethane / 0 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 12 h / Inert atmosphere
6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium methylate / methanol / 4 h / 0 °C
2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
4.1: triphenylphosphine; bromine / dichloromethane / 0 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 12 h / Inert atmosphere
6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C
7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux
8.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

propionic acid anhydride
123-62-6

propionic acid anhydride

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dipropionate
1453189-07-5

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dipropionate

Conditions
ConditionsYield
With sodium acetate; zinc at 130℃; for 0.5h;66%
With sodium acetate; zinc at 130℃; for 0.5h;66%
menaquinone-7
2124-57-4

menaquinone-7

benzoic acid anhydride
93-97-0

benzoic acid anhydride

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dibenzoate
1453189-00-8

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dibenzoate

Conditions
ConditionsYield
With sodium acetate; zinc at 140℃; for 1h;50%
Stage #1: menaquinone-7; benzoic acid anhydride With sodium acetate; zinc at 140℃; for 1h;
Stage #2: With diethylamine In tetrahydrofuran at 20℃; for 1h;
50%
menaquinone-7
2124-57-4

menaquinone-7

4-(trifluoromethyl)benzoic anhydride
25753-16-6

4-(trifluoromethyl)benzoic anhydride

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl bis(4-(trifluoromethyl)benzoate)
1453189-14-4

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl bis(4-(trifluoromethyl)benzoate)

Conditions
ConditionsYield
With sodium acetate; zinc at 170℃; for 23h;11%
Stage #1: menaquinone-7; 4-(trifluoromethyl)benzoic anhydride With sodium acetate; zinc at 170℃; for 23h;
Stage #2: With diethylamine In tetrahydrofuran at 20℃; for 1h;
11%
menaquinone-7
2124-57-4

menaquinone-7

acetic anhydride
108-24-7

acetic anhydride

1,4-diacetoxy-2-methyl-3-(3,7,11,15,19,23,27-heptamethyl-octacosaheptaen-(2t,6t,10t,14t,18t,22t,26)-yl)-naphthalene
122726-03-8

1,4-diacetoxy-2-methyl-3-(3,7,11,15,19,23,27-heptamethyl-octacosaheptaen-(2t,6t,10t,14t,18t,22t,26)-yl)-naphthalene

Conditions
ConditionsYield
With sodium acetate; zinc
With sodium acetate; zinc
menaquinone-7
2124-57-4

menaquinone-7

3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-2-methylnaphthalen-1-yl benzoate
1453189-02-0

3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-2-methylnaphthalen-1-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium acetate; zinc / 1 h / 140 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium acetate; zinc / 1 h / 140 °C
1.2: 1 h / 20 °C
2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-((diethoxyphosphoryl)oxy)-2-((2E,6E, 10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
1453189-03-1

4-((diethoxyphosphoryl)oxy)-2-((2E,6E, 10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 1 h / 140 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium acetate; zinc / 1 h / 140 °C
1.2: 1 h / 20 °C
2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-((diethoxyphosphoryl)oxy)-3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methylnaphthalen-1-yl benzoate
1453189-04-2

4-((diethoxyphosphoryl)oxy)-3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methylnaphthalen-1-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 1 h / 140 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium acetate; zinc / 1 h / 140 °C
1.2: 1 h / 20 °C
2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
1453189-05-3

4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 1 h / 140 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium acetate; zinc / 1 h / 140 °C
1.2: 1 h / 20 °C
2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-(((tert-butoxycarbonyl)-L-valyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
1453189-06-4

4-(((tert-butoxycarbonyl)-L-valyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 1 h / 140 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium acetate; zinc / 1 h / 140 °C
1.2: 1 h / 20 °C
2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl propionate
1453189-08-6

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl propionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-((diethoxyphosphoryl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate
1453189-10-0

4-((diethoxyphosphoryl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3: triethylamine / dichloromethane / 20 h / 0 - 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl (tert-butoxycarbonyl)-L-valinate

3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl (tert-butoxycarbonyl)-L-valinate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate
1453189-12-2

4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl 3-((tert-butoxycarbonyl)amino)propanoate
1453189-13-3

3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl 3-((tert-butoxycarbonyl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

4-((3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl)oxy)-4-oxobutanoic acid
1453189-15-5

4-((3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl)oxy)-4-oxobutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
3: dmap / dichloromethane / 3.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium acetate; zinc / 0.5 h / 130 °C
2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
3: dmap / dichloromethane / 3.5 h / 20 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl benzoate
1453189-01-9

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium acetate; zinc / 1 h / 140 °C
2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium acetate; zinc / 1 h / 140 °C
1.2: 1 h / 20 °C
2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C
View Scheme
menaquinone-7
2124-57-4

menaquinone-7

acetic anhydride
108-24-7

acetic anhydride

acetic acid 3-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-4-hydroxy-2-methyl-naphthalen-1-yl ester

acetic acid 3-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-4-hydroxy-2-methyl-naphthalen-1-yl ester

Conditions
ConditionsYield
With sodium acetate; zinc for 0.5h; Inert atmosphere; Reflux;

Vitamin K2(35) Specification

The CAS register number of Vitamin K2(35) is 2124-57-4. It also can be called 1,4-Naphthalenedione, 2-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosahept-aenyl)-3-methyl-, (all-E)- and the Systematic name about this chemical is 2-[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl]-3-methylnaphthalene-1,4-dione.

Physical properties about Vitamin K2(35) are: (1)ACD/LogP: 17.05; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 17.04; (4)ACD/LogD (pH 7.4): 17.04; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 20; (12)Polar Surface Area: 34.14Å2; (13)Index of Refraction: 1.532; (14)Molar Refractivity: 209.11 cm3; (15)Molar Volume: 674.7 cm3; (16)Surface Tension: 36 dyne/cm; (17)Density: 0.961 g/cm3; (18)Flash Point: 254.9 °C; (19)Enthalpy of Vaporization: 105.21 kJ/mol; (20)Boiling Point: 720.1 °C at 760 mmHg; (21)Vapour Pressure: 1.38E-20 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1.SMILES: O=C\2c1c(cccc1)C(=O)/C(=C/2C)C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C
2.InChI: InChI=1/C46H64O2/c1-34(2)18-12-19-35(3)20-13-21-36(4)22-14-23-37(5)24-15-25-38(6)26-16-27-39(7)28-17-29-40(8)32-33-42-41(9)45(47)43-30-10-11-31-44(43)46(42)48/h10-11,18,20,22,24,26,28,30-32H,12-17,19,21,23,25,27,29,33H2,1-9H3/b35-20+,36-22+,37-24+,38-26+,39-28+,40-32+ 
3.InChIKey: RAKQPZMEYJZGPI-LJWNYQGCBT
4.Std. InChI: InChI=1S/C46H64O2/c1-34(2)18-12-19-35(3)20-13-21-36(4)22-14-23-37(5)24-15-25-38(6)26-16-27-39(7)28-17-29-40(8)32-33-42-41(9)45(47)43-30-10-11-31-44(43)46(42)48/h10-11,18,20,22,24,26,28,30-32H,12-17,19,21,23,25,27,29,33H2,1-9H3/b35-20+,36-22+,37-24+,38-26+,39-28+,40-32+

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