Product Name

  • Name

    6-Cyano-2-naphthol

  • EINECS 628-663-7
  • CAS No. 52927-22-7
  • Article Data36
  • CAS DataBase
  • Density 1.28 g/cm3
  • Solubility
  • Melting Point 165.5-170.5 °C(lit.)
  • Formula C11H7NO
  • Boiling Point 383.1 °C at 760 mmHg
  • Molecular Weight 169.183
  • Flash Point 185.5 °C
  • Transport Information
  • Appearance brown crystalline solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 52927-22-7 (6-Cyano-2-naphthol)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Cyano-6-hydroxynaphthalene;2-Hydroxy-6-naphthonitrile;6-Cyano-2-hydroxynaphthalene;6-Hydroxy-2-naphthalenecarbonitrile;
  • PSA 44.02000
  • LogP 2.41708

Synthetic route

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate
939822-86-3

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 6h; Electrolysis; Green chemistry;94%
2-cyano-6-methoxynaphthalene
67886-70-8

2-cyano-6-methoxynaphthalene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
91%
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 10h;83%
With boron tribromide In dichloromethane at -78 - 20℃; for 16h; Inert atmosphere;69%
With sodium cyanide In dimethyl sulfoxide at 160 - 170℃; for 12h;62%
With boron tribromide
trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
145369-29-5

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 9h; Electrolysis; Green chemistry;91%
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With CuCN In N,N-dimethyl-formamide at 160 - 170℃; for 3h;83%
56%
In ethanol; N,N-dimethyl-formamide
In ethanol; N,N-dimethyl-formamide
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

copper(l) cyanide

copper(l) cyanide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 160 - 170℃; for 4h; Inert atmosphere;83%
In N,N-dimethyl-formamide at 135℃; for 18h;62%
In N,N-dimethyl-formamide at 150℃;60%
6-hydroxynaphthalene-2-carbaldehyde
78119-82-1

6-hydroxynaphthalene-2-carbaldehyde

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 1h;70%
6-acetoxy-[2]naphthonitrile
860363-16-2

6-acetoxy-[2]naphthonitrile

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With potassium hydroxide
acetate of α,α,α',α'-tetrabromo-3,4-xylenol
78119-72-9

acetate of α,α,α',α'-tetrabromo-3,4-xylenol

acrylonitrile
107-13-1

acrylonitrile

A

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

B

7-hydroxynaphthalene-2-carbonitrile
130200-58-7

7-hydroxynaphthalene-2-carbonitrile

Conditions
ConditionsYield
1) NaI, DMF; 2) hydrolysis; Yield given. Multistep reaction. Title compound not separated from byproducts;
benzoate of α,α,α',α'-tetrabromo-3,4-xylenol
78119-71-8

benzoate of α,α,α',α'-tetrabromo-3,4-xylenol

acrylonitrile
107-13-1

acrylonitrile

A

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

B

7-hydroxynaphthalene-2-carbonitrile
130200-58-7

7-hydroxynaphthalene-2-carbonitrile

Conditions
ConditionsYield
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction;
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction. Title compound not separated from byproducts;
6-bromonaphthalen-2-yl acetate
6343-72-2

6-bromonaphthalen-2-yl acetate

copper(I) cyanide
544-92-3

copper(I) cyanide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With pyridine; copper(II) sulfate In N,N-dimethyl-formamide
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

copper(I) cyanide
544-92-3

copper(I) cyanide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone at 160℃; for 3h; Substitution;
2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With boron tribromide demethylation;
3,4-dimethylphenyl benzoate
3845-63-4

3,4-dimethylphenyl benzoate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 12 h / Heating; Irradiation
2: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating
3: 1) NaI, DMF; 2) NaOH, CH3OH
View Scheme
Multi-step reaction with 2 steps
1: 88.5 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 25 h / Heating; Irradiation
2: 1) NaI, DMF; 2) NaOH, CH3OH
View Scheme
benzoate of α,α,α'-tribromo-3,4-xylenol

benzoate of α,α,α'-tribromo-3,4-xylenol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating
2: 1) NaI, DMF; 2) NaOH, CH3OH
View Scheme
6-bromonaphthalen-2-yl acetate
6343-72-2

6-bromonaphthalen-2-yl acetate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper (II)-sulfate; pyridine / 180 - 190 °C
2: methanol. KOH-solution
View Scheme
1-methyl-pyrrolidin-2-one
872-50-4

1-methyl-pyrrolidin-2-one

6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

iron(III) chloride

iron(III) chloride

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With hydrogenchloride; CaCl2 In water
C11H9NO2
1123760-79-1

C11H9NO2

A

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

B

6-cyano-1-naphthol
91059-47-1

6-cyano-1-naphthol

Conditions
ConditionsYield
With perchloric acid In water at 25℃; for 10h; Kinetics; Concentration;
β-naphthol
135-19-3

β-naphthol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine / acetic acid
1.2: 3 h / Reflux
2.1: N,N-dimethyl-formamide / 4 h / 160 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; tin; bromine / 3 h / Reflux
2: N,N-dimethyl-formamide / 4 h / 160 - 170 °C / Inert atmosphere
View Scheme
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C
1.2: 2 h / 20 °C
2.1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C
3.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
4.1: toluene-4-sulfonic acid / toluene / 16 h / Reflux
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
6.1: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-Methoxy-2-hydroxymethylen-1-tetralon
16252-53-2

6-Methoxy-2-hydroxymethylen-1-tetralon

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C
2: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
3: toluene-4-sulfonic acid / toluene / 16 h / Reflux
4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
5: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene
606494-99-9

1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / toluene / 16 h / Reflux
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
3: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile
34093-07-7

6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
2: toluene-4-sulfonic acid / toluene / 16 h / Reflux
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
4: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-methoxy-3,4-dihydronaphthalene-2-carbonitrile
79215-28-4

6-methoxy-3,4-dihydronaphthalene-2-carbonitrile

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
2: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-Hydroxy-2-naphthoic acid
16712-64-4

6-Hydroxy-2-naphthoic acid

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 70 °C
2.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C
3.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C
3.2: 16 h / 25 °C
View Scheme
6-hydroxynaphthalene-2-carboxamide
62529-01-5

6-hydroxynaphthalene-2-carboxamide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Stage #1: 6-hydroxynaphthalene-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 0 - 25℃; for 0.5h;
Stage #2: With pyridine In tetrahydrofuran at 25℃; for 16h;
C11H7ClO2

C11H7ClO2

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C
2.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C
2.2: 16 h / 25 °C
View Scheme
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 8h; Suzuki-Miyaura Coupling; High pressure; Inert atmosphere;
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-(aminomethyl)naphthalen-2-ol
199387-77-4

6-(aminomethyl)naphthalen-2-ol

Conditions
ConditionsYield
With ammonia; hydrogen; nickel In methanol; water100%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

D-cysteine hydrochloride
32443-99-5

D-cysteine hydrochloride

(S)-2-(6-hydroxynaphthalen-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
122364-82-3

(S)-2-(6-hydroxynaphthalen-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 80℃; for 5h;100%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

benzyl bromide
100-39-0

benzyl bromide

6-(benzyloxy)-2-cyanonaphthalene
66217-29-6

6-(benzyloxy)-2-cyanonaphthalene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;100%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

6-((4-methylbenzyl)oxy)-2-naphthonitrile

6-((4-methylbenzyl)oxy)-2-naphthonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;98%
1-Bromopentane
110-53-2

1-Bromopentane

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-(pentyloxy)-2-naphthonitrile

6-(pentyloxy)-2-naphthonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;98%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

(Z)-tert-butyl (3-methyl-5-oxo-1-phenyl-1H-pyrazol-4(5H)-ylidene) carbamate

(Z)-tert-butyl (3-methyl-5-oxo-1-phenyl-1H-pyrazol-4(5H)-ylidene) carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-phenyl-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-phenyl-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction;98%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

(Z)-tert-butyl (3-methyl-5-oxo-1-(p-tolyl)-1H-pyrazol-4(5H)-ylidene) carbamate

(Z)-tert-butyl (3-methyl-5-oxo-1-(p-tolyl)-1H-pyrazol-4(5H)-ylidene) carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-(p-tolyl)-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-(p-tolyl)-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction;98%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

6-p-tolyl-2-naphthonitrile
944042-22-2

6-p-tolyl-2-naphthonitrile

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;
Stage #2: 4-methylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;
97%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

5-benzhydryl-6-hydroxy-2-naphthonitrile

5-benzhydryl-6-hydroxy-2-naphthonitrile

Conditions
ConditionsYield
With stannic bromide In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; Inert atmosphere;97%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
145369-29-5

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 48h;95%
With triethylamine In dichloromethane at 20℃;93%
With pyridine In dichloromethane at 20℃;79.1%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

2,5,8,11-tetraoxatridecan-13-ol tosylate
62921-76-0

2,5,8,11-tetraoxatridecan-13-ol tosylate

tetraethylene glycol methyl 6-cyano-2-naphthyl ether

tetraethylene glycol methyl 6-cyano-2-naphthyl ether

Conditions
ConditionsYield
With potassium hydroxide In 1,2-dimethoxyethane at 80℃; for 16h; Williamson etherification;95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate
939822-86-3

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;95%
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;95%
Stage #1: 6-cyano-2-naphthol With triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 4h;
90%
With dmap; triethylamine In dichloromethane at 20℃;
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-(2-cyanonaphthalen-6-yl)benzoate
1290542-49-2

methyl 4-(2-cyanonaphthalen-6-yl)benzoate

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;
Stage #2: 4-methoxycarbonylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;
95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

6-(diphenylphosphoryl)-2-naphthonitrile
1378042-96-6

6-(diphenylphosphoryl)-2-naphthonitrile

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In acetonitrile at 100℃; for 3h; Inert atmosphere;
Stage #2: Diphenylphosphine oxide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In acetonitrile at 100℃; for 18h; Inert atmosphere;
95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

[(1,10-phenanthroline)2Cu][O2CCF2Cl]

[(1,10-phenanthroline)2Cu][O2CCF2Cl]

6-(difluoromethoxy)-2-naphthonitrile
1261682-37-4

6-(difluoromethoxy)-2-naphthonitrile

Conditions
ConditionsYield
With sodium hydroxide; phenol In N,N-dimethyl-formamide at 75℃; for 4h; Sealed tube; Inert atmosphere;95%
di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

C19H21N3O5

C19H21N3O5

Conditions
ConditionsYield
With 1,3,4-triphenyl-1,2,4-triazolium hexafluorophosphate; potassium tert-butylate In chloroform at 20℃; for 4h; Inert atmosphere;95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

1-bromo-7-(4-bromophenylthio)heptane

1-bromo-7-(4-bromophenylthio)heptane

1-(4-bromophenylthio)-7-(6-cyano-2-naphthyloxy)heptane

1-(4-bromophenylthio)-7-(6-cyano-2-naphthyloxy)heptane

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 12h; Williamson Ether Synthesis; Reflux;95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

6-cyanonaphthalen-2-yl methanesulfonate
939822-84-1

6-cyanonaphthalen-2-yl methanesulfonate

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With triethylamine In toluene at 0℃; for 0.166667h;
Stage #2: methanesulfonyl chloride In toluene at 20℃; for 12h;
93%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;91%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

allyl bromide
106-95-6

allyl bromide

6-(allyloxy)-2-naphthonitrile

6-(allyloxy)-2-naphthonitrile

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 70℃; for 4h;93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
1-bromo-butane
109-65-9

1-bromo-butane

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-(butyloxy)-2-naphthonitrile
66217-27-4

6-(butyloxy)-2-naphthonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;93%
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;93%
With potassium carbonate In acetonitrile at 80℃;93%
1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

2-(o-tolyl)naphtho[2,1-b]furan-7-carbonitrile

2-(o-tolyl)naphtho[2,1-b]furan-7-carbonitrile

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform; toluene at 80℃; for 2h; Inert atmosphere; Schlenk technique;93%
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
145369-29-5

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;93%
styrene
100-42-5

styrene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-isocyano-1-(1-phenylethyl)naphthalen-2-ol

6-isocyano-1-(1-phenylethyl)naphthalen-2-ol

Conditions
ConditionsYield
With phosphorous acid In water; 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; regioselective reaction;93%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

5-bromo-6-hydroxy-2-naphthonitrile
1192026-57-5

5-bromo-6-hydroxy-2-naphthonitrile

Conditions
ConditionsYield
With bromine; acetic acid at 20℃;92%
With bromine; acetic acid at 25℃; for 2.5h;
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere;
With pyridinium perbromide hydrobromide In acetonitrile at 0℃;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere; Schlenk technique;
1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate
866562-23-4

1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

(R)-2-methylene-1-phenyl-1,2-dihydronaphtho[2,1-b]furan-7-carbonitrile

(R)-2-methylene-1-phenyl-1,2-dihydronaphtho[2,1-b]furan-7-carbonitrile

Conditions
ConditionsYield
With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine In methanol at -20℃; for 12h; Schlenk technique; Inert atmosphere; enantioselective reaction;92%
Stage #1: 1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate; 6-cyano-2-naphthol With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate In methanol for 1h; Inert atmosphere;
Stage #2: With N-ethyl-N,N-diisopropylamine In methanol for 24h; Inert atmosphere;
90%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

C10H9BrOS2

C10H9BrOS2

1-(3-bromobenzoyl)-2-(methylthio)-4,5-dioxo-4,5-dihydronaphtho[2,1-b]thiophene-8-carbonitrile

1-(3-bromobenzoyl)-2-(methylthio)-4,5-dioxo-4,5-dihydronaphtho[2,1-b]thiophene-8-carbonitrile

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) bis(trifluoromethanesulfonate) In acetic acid at 100℃; for 0.166667h;
Stage #2: C10H9BrOS2 In acetic acid at 100℃; for 4h; chemoselective reaction;
92%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride
68641-49-6

bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride

6-cyanonaphthalen-2-yl bis(2-oxo-3-oxazolidinyl)phosphoramide
1231261-78-1

6-cyanonaphthalen-2-yl bis(2-oxo-3-oxazolidinyl)phosphoramide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;91%

6-Cyano-2-Naphthol Chemical Properties

Molecular Structure of 6-Cyano-2-Naphthol (CAS NO.52927-22-7):

Molecular Formula: C11H7NO
Molar mass: 169.17938g/mol
Density: 1.28 g/cm3
Flash Point: 185.5 °C
Melting point: 165.5-170.5 °C
Appearance: Brown Crystalline Solid
Boiling Point: 383.1 °C at 760 mmHg
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 33.02Å2
Index of Refraction: 1.692
Molar Refractivity: 50.4 cm3
Molar Volume: 131.5 cm3
Surface Tension: 64.7 dyne/cm
Enthalpy of Vaporization: 65.64 kJ/mol
Vapour Pressure: 2.04E-06 mmHg at 25°C
Product Categoriy: Aromatics and Nitrogen Compounds; Cyanides/Nitriles; Chalcones; Functional Materials

6-Cyano-2-Naphthol Safety Profile

Hazard Codes: Xi
Risk Statements:
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing
WGK Germany: 3

6-Cyano-2-Naphthol Specification

  6-Cyano-2-Naphthol , with CAS number of 52927-22-7, can be called 6-Hydroxy-2-naphthalenecarbonitrile ; 2-Cyano-6-hydroxynaphthalene ; 2-Hydroxy-6-naphthonitrile . 6-Cyano-2-Naphthol (CAS NO.52927-22-7) is functional Material,and can be used for building blocks forliquid crystals.

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