Product Name

  • Name

    Gemfibrozil

  • EINECS 247-280-2
  • CAS No. 25812-30-0
  • Article Data19
  • CAS DataBase
  • Density 1.044 g/cm3
  • Solubility >0.5g/L(temperature not stated)
  • Melting Point 61-63 °C
  • Formula C15H22O3
  • Boiling Point 394.7 °C at 760 mmHg
  • Molecular Weight 250.338
  • Flash Point 141.6 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 36-53-36/37-26-25
  • Risk Codes 22-63-62-46-36/38-21
  • Molecular Structure Molecular Structure of 25812-30-0 (Gemfibrozil)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure;Lipira;Normolip;2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid;Valeric acid, 2,2-dimethyl-5-(2,5-xylyloxy)-;WL-Gemfibrozil;Gozid;Litarek;Gemfibrozilum [INN-Latin];Pentanoic acid,5-(2,5-dimethylphenoxy)-2,2- dimethyl-;Apo-Gemfibrozil;Lipazil;Regulip;Lanaterom;Gemfibromax;Low-Lip;Gevilon Uno;Gemfibrozil [USAN:BAN:INN];Decrelip;Taborcil;Micolip;CI 719;Lifibron;Sinelip;Ipolipid;Reducel;2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure;Gemfibrozil (JAN/USP);CI-719;Fibratol;Jezil;Brozil;Gemfibrozilo [INN-Spanish];Hipolixan;Gemd;Pilder;Gem-S;Lipur;5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid;Fibrocit;Lopid;Pentanoic acid, 5-(2,5-dimethylphenoxy)-2,2-dimethyl-;Ausgem;Gemnpid;Clearol;
  • PSA 46.53000
  • LogP 3.57320

Synthetic route

2,2-dimethyl-5-(2,5-dimethylphenoxy)-3-hydroxypentanoic acid β-lactone
169295-45-8

2,2-dimethyl-5-(2,5-dimethylphenoxy)-3-hydroxypentanoic acid β-lactone

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With sodium tetrahydroborate In N,N-dimethyl-formamide for 12h; Ambient temperature;90%
1,3-Bis[2.2-dimethyl-5-(2,5-dimethylphenoxy)-pentanoyloxy]-propane
139483-63-9

1,3-Bis[2.2-dimethyl-5-(2,5-dimethylphenoxy)-pentanoyloxy]-propane

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether; ethanol; water82%
methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With tetrabutylammomium bromide; water; sodium hydroxide at 73 - 75℃; for 3h; Inert atmosphere;77.6%
With sodium hydroxide In dimethyl sulfoxide; toluene for 4h;860 mg
5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal
39938-97-1

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; under 760.051 Torr; for 10h; Schlenk technique;72%
With potassium carbonate In n-heptane; water
carbon monoxide
201230-82-2

carbon monoxide

5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With copper(I) oxide; sulfuric acid at -12 - -8℃; for 1.5h;56%
carbon monoxide
201230-82-2

carbon monoxide

2-methyl-5-(2,5-dimethylphenoxy)-2-pentene
172533-96-9

2-methyl-5-(2,5-dimethylphenoxy)-2-pentene

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With copper(I) oxide; sulfuric acid at -12 - -8℃;47%
carbon monoxide
201230-82-2

carbon monoxide

5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

A

gemfibrozil
25812-30-0

gemfibrozil

B

2,2-dimethyl-5-(2,5-dimethyl-4-sulfophenoxy)pentanoic acid

2,2-dimethyl-5-(2,5-dimethyl-4-sulfophenoxy)pentanoic acid

Conditions
ConditionsYield
With copper(I) oxide; sulfuric acid at 0 - 5℃; for 4h;A n/a
B 2.0 g
...Expand
carbon monoxide
201230-82-2

carbon monoxide

2-methyl-5-(2,5-dimethylphenoxy)-2-pentene
172533-96-9

2-methyl-5-(2,5-dimethylphenoxy)-2-pentene

A

gemfibrozil
25812-30-0

gemfibrozil

B

2,2-dimethyl-5-(2,5-dimethyl-4-formylphenoxy)pentanoic acid

2,2-dimethyl-5-(2,5-dimethyl-4-formylphenoxy)pentanoic acid

Conditions
ConditionsYield
With sulfuric acid at -16℃; for 24h;A 3.5 g
B 1.5 g
...Expand
5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66.9 percent / potassium bisulfite / 1.) from 50 to 60 deg C, 5 Torr, 5 min, 2.) from 60 to 120 deg C, 20 min
2: 47 percent / 1.) 98percent H2SO4, Cu2O / -12 - -8 °C
View Scheme
Multi-step reaction with 2 steps
1: 66.9 percent / potassium bisulfite / 1.) from 50 to 60 deg C, 5 Torr, 5 min, 2.) from 60 to 120 deg C, 20 min
2: 3.5 g / 98percent H2SO4 / 24 h / -16 °C
View Scheme
2,5-Dimethylphenol
95-87-4

2,5-Dimethylphenol

1-p-xylyl-4-methyl-1.2.3-triazole

1-p-xylyl-4-methyl-1.2.3-triazole

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / aq. NaOH, tetrabutylammonium hydroxide / 24 h / Heating
2: 90 percent / aq. p-TsOH / ethyl acetate / 60 °C
3: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C
4: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / aq. NaOH, tetrabutylammonium hydroxide / Heating
2: aq. p-TsOH / ethyl acetate / 0.75 h / 60 °C
3: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C
4: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature
View Scheme
3-(2,5-Dimethylphenoxy)-propionaldehyde
164917-45-7

3-(2,5-Dimethylphenoxy)-propionaldehyde

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C
2: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature
View Scheme
3-(2,5-dimethylphenoxy)propanal dimethylacetal

3-(2,5-dimethylphenoxy)propanal dimethylacetal

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / aq. p-TsOH / ethyl acetate / 60 °C
2: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C
3: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature
View Scheme
3-(2,5-dimethylphenoxy)propanal diethylacetal
1025804-42-5

3-(2,5-dimethylphenoxy)propanal diethylacetal

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. p-TsOH / ethyl acetate / 0.75 h / 60 °C
2: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C
3: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature
View Scheme
2,5-Dimethylphenol
95-87-4

2,5-Dimethylphenol

1,3-bis(2,2-dimethyl-5-chloropentanoyloxy)-propane
139483-62-8

1,3-bis(2,2-dimethyl-5-chloropentanoyloxy)-propane

butan-1-ol
71-36-3

butan-1-ol

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With sodium hydroxide In hexane; water
...Expand
2,5-Dimethylphenol
95-87-4

2,5-Dimethylphenol

1,3-bis(2,2-dimethyl-5-chloropentanoyloxy)-propane
139483-62-8

1,3-bis(2,2-dimethyl-5-chloropentanoyloxy)-propane

A

propane-1,3-diyl bis(2-methylpropanoate)

propane-1,3-diyl bis(2-methylpropanoate)

B

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With sodium hydroxide; sodium iodide In N-methyl-acetamide; water
With sodium hydroxide; sodium iodide; dimethyl sulfoxide In hexane; water; toluene
...Expand
2,5-Dimethylphenol
95-87-4

2,5-Dimethylphenol

methyl 5-chloro-2,2-dimethylpentanoate
73441-42-6

methyl 5-chloro-2,2-dimethylpentanoate

5-(2,5-Dimethylphenoxy-2,2-dimethylpentanoci Acid

5-(2,5-Dimethylphenoxy-2,2-dimethylpentanoci Acid

gemfibrozil
25812-30-0

gemfibrozil

...Expand
C23H29NO5
1313480-49-7

C23H29NO5

A

nicotinic acid
59-67-6

nicotinic acid

B

2-Hydroxyethyl nicotinate
3612-80-4

2-Hydroxyethyl nicotinate

C

gemfibrozil
25812-30-0

gemfibrozil

D

2-hydroxyethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate
1313404-96-4

2-hydroxyethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

E

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
With hydrogenchloride at 37℃; pH=7.4; Kinetics; aq. phosphate buffer; Enzymatic reaction;
...Expand
isobutyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate
149105-26-0

isobutyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

A

gemfibrozil
25812-30-0

gemfibrozil

B

C30H42O6
1446438-83-0

C30H42O6

C

C22H34O5
1446438-84-1

C22H34O5

Conditions
ConditionsYield
Stage #1: isobutyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate With sodium hydroxide In toluene at 100 - 112℃; for 7h;
Stage #2: With water at 70 - 80℃;		A 127.5 g
B n/a
C n/a
...Expand
2,2-dimethylpent-4-enoic acid
16386-93-9

2,2-dimethylpent-4-enoic acid

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dibenzoyl peroxide; hydrogen bromide / hexane / 5 h / 0 - 5 °C
2: sulfuric acid / 16 h / 60 - 70 °C
3: potassium carbonate; tetrabutylammomium bromide / toluene / 18 h / 110 °C / Inert atmosphere
4: tetrabutylammomium bromide; water; sodium hydroxide / 3 h / 73 - 75 °C / Inert atmosphere
View Scheme
2,2-dimethyl-5-bromopentanoic acid
82884-95-5

2,2-dimethyl-5-bromopentanoic acid

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / 16 h / 60 - 70 °C
2: potassium carbonate; tetrabutylammomium bromide / toluene / 18 h / 110 °C / Inert atmosphere
3: tetrabutylammomium bromide; water; sodium hydroxide / 3 h / 73 - 75 °C / Inert atmosphere
View Scheme
4-[(E)-2-phenylvinyl]phenyl-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

4-[(E)-2-phenylvinyl]phenyl-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

A

gemfibrozil
25812-30-0

gemfibrozil

B

trans-4-Hydroxystilbene
6554-98-9

trans-4-Hydroxystilbene

Conditions
ConditionsYield
With sodium hydroxide In ethanol
4-methylsalicylaldehyde
698-27-1

4-methylsalicylaldehyde

2,2-dimethyl-5-bromopentanoic acid
82884-95-5

2,2-dimethyl-5-bromopentanoic acid

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 3h; Reflux;
2,5-Dimethylphenol
95-87-4

2,5-Dimethylphenol

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / toluene; dimethyl sulfoxide / 2 h / Reflux
1.2: 110 °C
2.1: sodium hydroxide / toluene; dimethyl sulfoxide / 4 h
View Scheme
methyl 5-chloro-2,2-dimethylpentanoate
73441-42-6

methyl 5-chloro-2,2-dimethylpentanoate

gemfibrozil
25812-30-0

gemfibrozil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / toluene; dimethyl sulfoxide / 2 h / Reflux
1.2: 110 °C
2.1: sodium hydroxide / toluene; dimethyl sulfoxide / 4 h
View Scheme
gemfibrozil
25812-30-0

gemfibrozil

1,4-dimethyl-2-((4-methylpent-4-en-1-yl)oxy)benzene

1,4-dimethyl-2-((4-methylpent-4-en-1-yl)oxy)benzene

Conditions
ConditionsYield
With 9-(2-chlorophenyl)acridine; chloropyridinecobaloxime(III) In dichloromethane; acetonitrile at 25 - 27℃; for 36h; Irradiation; regioselective reaction;99%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

gemfibrozil
25812-30-0

gemfibrozil

1,3-dioxoisoindolin-2-yl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

1,3-dioxoisoindolin-2-yl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; Inert atmosphere;98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;94%
gemfibrozil
25812-30-0

gemfibrozil

5-(4-iodo-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

5-(4-iodo-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

Conditions
ConditionsYield
With iodine; oxygen; 9,10-phenanthrenequinone; trifluoroacetic acid In benzene at 25℃; for 1h; Irradiation; regioselective reaction;98%
2,2'-dipyridyldisulphide
2127-03-9

2,2'-dipyridyldisulphide

gemfibrozil
25812-30-0

gemfibrozil

C20H25NO2S

C20H25NO2S

Conditions
ConditionsYield
With triphenylphosphine In acetonitrile for 3h; Reflux;98%
gemfibrozil
25812-30-0

gemfibrozil

2-(3-(2,5-dimethylphenoxy)propyl)-2-methylpropionyl chloride
79791-29-0

2-(3-(2,5-dimethylphenoxy)propyl)-2-methylpropionyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h;97.5%
With thionyl chloride In dichloromethane at 40℃; for 1h; Inert atmosphere;72.9%
With oxalyl dichloride In dichloromethane at 0 - 20℃; Inert atmosphere;
gemfibrozil
25812-30-0

gemfibrozil

5-(2,5-dimethylphenoxy)-2,2-dimethylpentan-1-ol
39938-64-2

5-(2,5-dimethylphenoxy)-2,2-dimethylpentan-1-ol

Conditions
ConditionsYield
Stage #1: gemfibrozil With borane-THF In tetrahydrofuran at 0 - 20℃; for 17h;
Stage #2: With water In tetrahydrofuran		97%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 17h;97%
With lithium aluminium tetrahydride In tetrahydrofuran at 70℃; for 12h; Cooling with ice;65.3%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 70℃; for 12h;37%
gemfibrozil
25812-30-0

gemfibrozil

bromopentene
1119-51-3

bromopentene

pent-4-en-1-yl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

pent-4-en-1-yl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Inert atmosphere;97%
gemfibrozil
25812-30-0

gemfibrozil

imino(methyl)(pyridin-2-yl)-λ6-sulfanone
76456-06-9

imino(methyl)(pyridin-2-yl)-λ6-sulfanone

N-[5-(2,5-dmethylphenoxy)-2,2-dimethylpentanoyl]-S-methyl-S-2-pyridylsulfoximine
1384980-57-7

N-[5-(2,5-dmethylphenoxy)-2,2-dimethylpentanoyl]-S-methyl-S-2-pyridylsulfoximine

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;96%
gemfibrozil
25812-30-0

gemfibrozil

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

C24H38N2O4

C24H38N2O4

Conditions
ConditionsYield
Stage #1: gemfibrozil With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 5.5h; Cooling with ice;
Stage #2: 1-t-Butoxycarbonylpiperazine With triethylamine In dichloromethane for 12h; Cooling with ice;		96%
gemfibrozil
25812-30-0

gemfibrozil

methyl 4-chloro-2-methylenebutanoate

methyl 4-chloro-2-methylenebutanoate

methyl 1-(5-(2,5-dimethylphenoxy)-2,2-dimethylpentyl)cyclopropane-1-carboxylate

methyl 1-(5-(2,5-dimethylphenoxy)-2,2-dimethylpentyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In N,N-dimethyl-formamide for 20h; Sealed tube; Irradiation;95%
gemfibrozil
25812-30-0

gemfibrozil

methyl iodide
74-88-4

methyl iodide

methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;94%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;85%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;79%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;64.8%
gemfibrozil
25812-30-0

gemfibrozil

5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylvaleric acid
1374011-92-3

5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylvaleric acid

Conditions
ConditionsYield
With N-chloro-succinimide; dimethyl sulfoxide In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique;93%
With sodium hypochlorite In methanol; water
gemfibrozil
25812-30-0

gemfibrozil

C15H20O3

C15H20O3

Conditions
ConditionsYield
With tert.-butylhydroperoxide; N-acetyl-3-amino-2-methylpropanoic acid; sodium acetate; palladium diacetate In decane at 60℃; for 12h;93%
With tert.-butylhydroperoxide; N-acetyl-β-alanine; sodium acetate; palladium diacetate In water at 20 - 60℃; for 24.0833h; Sealed tube;
gemfibrozil
25812-30-0

gemfibrozil

2-bromoethanol
540-51-2

2-bromoethanol

2-hydroxyethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate
1313404-96-4

2-hydroxyethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;90.54%
gemfibrozil
25812-30-0

gemfibrozil

1-benzotriazolecarboxylic acid chloride
65095-13-8

1-benzotriazolecarboxylic acid chloride

gemfibrozil 1-benzotriazolide
288576-82-9

gemfibrozil 1-benzotriazolide

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 2.5h;89.2%
gemfibrozil
25812-30-0

gemfibrozil

4-chlorobenzoylmethyl bromide
536-38-9

4-chlorobenzoylmethyl bromide

2-(4-chlorophenyl)-2-oxoethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

2-(4-chlorophenyl)-2-oxoethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;89.2%
gemfibrozil
25812-30-0

gemfibrozil

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanamide

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanamide

Conditions
ConditionsYield
Stage #1: gemfibrozil With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h;
Stage #2: With ammonia In dichloromethane at 0℃; for 0.5h;		88.6%
Stage #1: gemfibrozil With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;
Stage #2: With ammonia In dichloromethane at 0℃; for 0.5h;		88.6%
gemfibrozil
25812-30-0

gemfibrozil

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal
39938-97-1

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal

Conditions
ConditionsYield
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction;88%
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 17 h / 0 - 20 °C
2: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 17 h / 0 - 20 °C
2: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C
View Scheme
Stage #1: gemfibrozil With 2,6-dimethylpyridine; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate for 0.25h; Inert atmosphere; Green chemistry;
Stage #2: With diphenylsilane In ethyl acetate at 60℃; for 16h; Inert atmosphere; Green chemistry;		196 mg
gemfibrozil
25812-30-0

gemfibrozil

N-methyl-tetrachlorophthalimide
14737-80-5

N-methyl-tetrachlorophthalimide

4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;88%
gemfibrozil
25812-30-0

gemfibrozil

2-phenyl-acrylic acid methyl ester
1865-29-8

2-phenyl-acrylic acid methyl ester

methyl 7-(2,5-dimethylphenoxy)-4,4-dimethyl-2-phenylheptanoate

methyl 7-(2,5-dimethylphenoxy)-4,4-dimethyl-2-phenylheptanoate

Conditions
ConditionsYield
With titanium(IV) dioxide In acetonitrile for 48h; Inert atmosphere; Irradiation; Cooling;87%
gemfibrozil
25812-30-0

gemfibrozil

ethylenediamine
107-15-3

ethylenediamine

2C15H22O3*C2H8N2

2C15H22O3*C2H8N2

Conditions
ConditionsYield
In water at 20℃; for 2h;86%
methanol
67-56-1

methanol

gemfibrozil
25812-30-0

gemfibrozil

methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

Conditions
ConditionsYield
With sulfuric acid for 1h; Reflux;86%
With sulfuric acid Reflux;84%
With sulfuric acid at 80℃; for 16h; Inert atmosphere;
With sulfuric acid
gemfibrozil
25812-30-0

gemfibrozil

1-deutero-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal

1-deutero-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal

Conditions
ConditionsYield
Stage #1: gemfibrozil With 2,6-dimethylpyridine; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate for 0.25h; Inert atmosphere; Green chemistry;
Stage #2: With dideuteriodiphenylsilane In ethyl acetate at 60℃; for 16h; Inert atmosphere; Green chemistry;		86%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

gemfibrozil
25812-30-0

gemfibrozil

benzaldehyde
100-52-7

benzaldehyde

7-(2,5-dimethylphenoxy)-4,4-dimethyl-1,2,2-triphenylheptan-1-ol

7-(2,5-dimethylphenoxy)-4,4-dimethyl-1,2,2-triphenylheptan-1-ol

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; sodium carbonate In dimethyl sulfoxide at 23 - 25℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;86%
...Expand
gemfibrozil
25812-30-0

gemfibrozil

α-bromoacetophenone
70-11-1

α-bromoacetophenone

2-oxo-2-phenylethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

2-oxo-2-phenylethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;85.2%
gemfibrozil
25812-30-0

gemfibrozil

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

C18H27BrO3

C18H27BrO3

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;85%
gemfibrozil
25812-30-0

gemfibrozil

2-Bromo-4'-methoxyacetophenone
2632-13-5

2-Bromo-4'-methoxyacetophenone

2-(4-methoxyphenyl)-2-oxoethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

2-(4-methoxyphenyl)-2-oxoethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;84.2%
gemfibrozil
25812-30-0

gemfibrozil

benzylacrylate
2495-35-4

benzylacrylate

benzyl 7-(2,5-dimethylphenoxy)-4,4-dimethylheptanoate

benzyl 7-(2,5-dimethylphenoxy)-4,4-dimethylheptanoate

Conditions
ConditionsYield
With piperazine; 9-(2-chlorophenyl)acridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 25 - 27℃; for 14h; Irradiation;84%
gemfibrozil
25812-30-0

gemfibrozil

4-(bromoacetyl)toluene
619-41-0

4-(bromoacetyl)toluene

2-oxo-2-(p-tolyl)ethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

2-oxo-2-(p-tolyl)ethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;83.7%

Gemfibrozil Specification

1. Introduction of Gemfibrozil
Gemfibrozil is one kind of white or off-white crystalline powder. The IUPAC Name of this chemical is 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid. It belongs to Active Pharmaceutical Ingredients;APIs;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Intracellular receptor. 

The Classification Code of Gemfibrozil is Antihyperlipidemic; Antilipemic agents; Antimetabolites; Drug / Therapeutic Agent; Human Data; Hypolipidemic Agents; Lipid Regulating Agents; Reproductive Effect; Tumor data.

2. Properties of Gemfibrozil
Physical properties about Gemfibrozil are:
(1)Melting point: 61-63 °C; (2)Index of Refraction: 1.511; (3)Density: 1.044 g/cm3; (4)Flash Point: 141.6 °C; (5)Enthalpy of Vaporization: 68 kJ/mol; (6)Boiling Point: 394.7 °C at 760 mmHg; (7)Vapour Pressure: 6.13E-07 mmHg at 25 °C; (8)Appearance: White crystalline powder; (9)XLogP3-AA: 3.8; (10)H-Bond Donor: 1; (11)H-Bond Acceptor: 3.

3. Structure Descriptors of Gemfibrozil
(1)InChI: InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)
(2)InChIKey: InChIKey=HEMJJKBWTPKOJG-UHFFFAOYSA-N
(3)Smiles: c1(c(ccc(c1)C)C)OCCCC(C(O)=O)(C)C

4. Toxicity of Gemfibrozil

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25, Pg. 699, 1997.
man TDLo oral 18gm/kg/3Y-I (18000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 Archives of Internal Medicine. Vol. 151, Pg. 1873, 1991.
mouse LD50 oral 2218mg/kg (2218mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toksikologicheskii Vestnik. Vol. (6), Pg. 38, 1995.
rat LD50 intraperitoneal 445mg/kg (445mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toksikologicheskii Vestnik. Vol. (6), Pg. 38, 1995.
rat LD50 oral 1414mg/kg (1414mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25, Pg. 645, 1997.

5. Physical Properties of Gemfibrozil

Physical Property Value Units Temp (deg C) Source
Melting Point 62 deg C   EXP
log P (octanol-water) 4.770 (none)   EST
Atmospheric OH Rate Constant 8.24E-11 cm3/molecule-sec 25 EST

Or

1.    

orl-rat LD50:4786 mg/kg

     PRSMA4    Proceedings of the Royal Society of Medicine. 69 (Suppl 2)(1976),15.
2.    

orl-mus LD50:3162 mg/kg

     PRSMA4    Proceedings of the Royal Society of Medicine. 69 (Suppl 2)(1976),15.

6. Safety information of Gemfibrozil 
 Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-63-62-46-36/38-21 
R21:Harmful in contact with skin. 
R22:Harmful if swallowed. 
R36/38:Irritating to eyes and skin. 
R46:May cause heritable genetic damage. 
R62:Risk of impaired fertility. 
R63:Possible risk of harm to the unborn child.
Safety Statements: 36-53-36/37-26-25 
S25:Avoid contact with eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S36/37:Wear suitable protective clothing and gloves. 
S53:Avoid exposure - obtain special instructions before use.

7. Uses of Gemfibrozil
Gemfibrozil (CAS NO.25812-30-0) is a serum lipid regulating agent used as an  antihyperlipoproteinemic. It is a serum lipid regulating agent used as an antihyperlipoproteinemic. Gemfibrozil helps reduce cholesterol and triglycerides (fatty acids) in the blood. High levels of these types of fat in the blood are associated with an increased risk of atherosclerosis (clogged arteries).

8. Production of Gemfibrozil
(1)2,5-Dimethylphenol and 1-Bromo-3-chloropropane reaction of 1-(2,5-dimethylphenoxy)-3-chloropropane. The reaction is carried out in toluene, adding new clean off reflux 5h. Just as follows:

Production of Gemfibrozil

(2)N/A can be used to manufacture Gemfibrozil.

Production of Gemfibrozil

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