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Ciprofibrate is a potent, long-acting hypolipidemic agent related to clofibrate, bezafibrate, and fenofibrate. It is an agonist of peroxisome proliferator-activated receptor α (PPARα) and is effective in treating various types of hyperlipoproteinemias. Ciprofibrate is characterized as an off-white to pale beige solid and is available under the brand name LJPANOR.

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  • 52214-84-3 Structure
  • Basic information

    1. Product Name: Ciprofibrate
    2. Synonyms: 2-(p-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropionicacid;2-[4-(2,2-Dichlom-cyclopropyl)phenoxy]-2-methy|propanoic acid;Cipml;Lipanor;Modalim;Win-35833;2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic acid;Ciprofibric acid
    3. CAS NO:52214-84-3
    4. Molecular Formula: C13H14Cl2O3
    5. Molecular Weight: 289.15
    6. EINECS: 257-744-6
    7. Product Categories: Intracellular receptor;API
    8. Mol File: 52214-84-3.mol
  • Chemical Properties

    1. Melting Point: 114-116°
    2. Boiling Point: 401.74°C (rough estimate)
    3. Flash Point: 210.7 °C
    4. Appearance: White or almost white powder
    5. Density: 1.2576 (rough estimate)
    6. Vapor Pressure: 5.63E-08mmHg at 25°C
    7. Refractive Index: 1.5209 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: Practically insoluble in water, freely soluble in anhydrous ethanol, soluble in toluene.
    10. PKA: 3.31±0.10(Predicted)
    11. Merck: 14,2313
    12. CAS DataBase Reference: Ciprofibrate(CAS DataBase Reference)
    13. NIST Chemistry Reference: Ciprofibrate(52214-84-3)
    14. EPA Substance Registry System: Ciprofibrate(52214-84-3)
  • Safety Data

    1. Hazard Codes: T
    2. Statements: 45
    3. Safety Statements: 53-22-36/37/39-45
    4. WGK Germany: 3
    5. RTECS: UF0880000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 52214-84-3(Hazardous Substances Data)

52214-84-3 Usage

Uses

Used in Pharmaceutical Industry:
Ciprofibrate is used as an antilipemic agent for the treatment of dyslipidemia. It activates PPARα, which results in the expression of genes involved in fatty acid β-oxidation, binding, and transport, thus helping to regulate lipid homeostasis.
Used in Treatment of Hypertriglyceridemia:
Ciprofibrate is used as a hypolipemic agent for the treatment of hypertriglyceridemia. It decreases fasting plasma levels of triglycerides and increases fasting plasma glucose levels in the apolipoprotein CIII transgenic mouse model when administered at a dose of 10 mg/kg.
Used in Treatment of Hyperlipoproteinemias:
Ciprofibrate is used as a hypolipidemic agent for the treatment of types IIa, IIb, IIX, and IV hyperlipoproteinemias. It produces a beneficial elevation of the anti-atherogenic HDL, contributing to the prevention of atherosclerosis.
Used in Activation of PPARα:
Ciprofibrate is used as a selective agonist for PPARα over PPARγ and PPARδ at 300 μM. It activates PPARα with an EC50 value of 20 μM, which helps in the regulation of lipid homeostasis and the treatment of dyslipidemia.
Used in Indirect Reverse Cholesterol Transport System:
Ciprofibrate reportedly stimulates cholesteryl ester transfer protein expression and improves the flow of cholesterol through the indirect reverse cholesterol transport system, preserving plasma HDL and contributing to the prevention of atherosclerosis.

Originator

Sterling-Wintbrop (USA)

Manufacturing Process

A mixture of 8 g (0.0356 mol) of p-(2,2-dichlorocyclopropyl)phenol, 11.2 g (0.28 mol) of sodium hydroxide pellets, 11 g of chloroform and 350 ml of acetone was prepared at 0°C. The cooling bath was removed, the mixture stirred for a minute and then heated on a steam bath to reflux temperature. The reaction mixture was stirred at reflux for three hours and then concentrated in vacuo. The residual gum was partitioned between dilutehydrochloric acid and ether, and the ether layer was separated, dried and concentrated in vacuo. The residual oil (14 g) was partitioned between dilute aqueous sodium bicarbonate and ether. The sodium bicarbonate solution was acidified with concentrated hydrochloric acid and extracted with ether. The ether solution was dried over anhydrous sodium sulfate and concentrated. The residue (9.5 g of yellow oil) was crystallized twice from hexane to give 6.0 g of 2-[p-(2,2-dichlorocyclopropyl)phenoxy]-2-methyl propionic acid in the form of a pale cream-colored solid, MP 114°C to 116°C.

Therapeutic Function

Antihyperlipidemic

World Health Organization (WHO)

The safety profile of ciprofibrate is similar to that of clofibrate. See also under clofibrate in full edition.

Biochem/physiol Actions

Peroxisome proliferator-activated receptor α (PPARα) agonist

Drug interactions

Potentially hazardous interactions with other drugs Antibacterials: increased risk of myopathy with daptomycin - try to avoid concomitant use. Anticoagulants: enhances effect of coumarins and phenindione. Dose of anticoagulant should be reduced by up to 50% and readjusted by monitoring INR. Antidiabetics: may improve glucose tolerance and have an additive effect with insulin or sulphonylureas. Colchicine: possible increased risk of myopathy. Lipid-regulating drugs: increased risk of myopathy in combination with statins and ezetimibe (Do not exceed 10 mg of simvastatin and 20 mg of rosuvastatin.1 ) - avoid with ezetimibe.

Metabolism

Approximately 30-75% of a single dose administered to volunteers was excreted in the urine in 72 hours, either as unchanged ciprofibrate (20-25% of the total excreted) or as a glucuronide conjugate. Subjects with moderate renal impairment excreted on average 7% of a single dose as unchanged ciprofibrate over 96 hours, compared with 6.9% in normal subjects. In subjects with severe insufficiency this was reduced to 4.7%.

Check Digit Verification of cas no

The CAS Registry Mumber 52214-84-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,2,1 and 4 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 52214-84:
(7*5)+(6*2)+(5*2)+(4*1)+(3*4)+(2*8)+(1*4)=93
93 % 10 = 3
So 52214-84-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H14Cl2O3/c1-12(2,11(16)17)18-9-5-3-8(4-6-9)10-7-13(10,14)15/h3-6,10H,7H2,1-2H3,(H,16,17)

52214-84-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (C2667)  Ciprofibrate  >98.0%(GC)(T)

  • 52214-84-3

  • 1g

  • 690.00CNY

  • Detail
  • TCI America

  • (C2667)  Ciprofibrate  >98.0%(GC)(T)

  • 52214-84-3

  • 5g

  • 2,450.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000362)  Ciprofibrate  European Pharmacopoeia (EP) Reference Standard

  • 52214-84-3

  • Y0000362

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000363)  Ciprofibrate for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 52214-84-3

  • Y0000363

  • 1,880.19CNY

  • Detail
  • Sigma

  • (C0330)  Ciprofibrate  

  • 52214-84-3

  • C0330-10MG

  • 1,481.22CNY

  • Detail
  • Sigma

  • (C0330)  Ciprofibrate  

  • 52214-84-3

  • C0330-25MG

  • 3,143.79CNY

  • Detail

52214-84-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ciprofibrate

1.2 Other means of identification

Product number -
Other names 2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:52214-84-3 SDS

52214-84-3Synthetic route

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate
130232-51-8, 130233-23-7, 130233-24-8

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 0.5h;92%
With sodium hydroxide In ethanol; water at 20℃; for 0.5h; pH=3 - 4; Solvent; Large scale;91%
ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionate
52179-28-9, 144940-19-2, 144940-25-0

ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionate

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; for 0.5h;90%
(-)-4-(2,2-dichlorocyclopropyl)phenol
52179-26-7, 135133-52-7, 135133-54-9

(-)-4-(2,2-dichlorocyclopropyl)phenol

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide In chloroform; acetone
With sodium hydroxide
4-Vinylphenol
2628-17-3

4-Vinylphenol

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 48 h / 20 °C
2: trimethyldodecylammonium chloride; sodium hydroxide / 24 h / 20 °C
3: sodium hydroxide / methanol; water / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: caesium carbonate / acetonitrile / 24 h / 20 °C
2: sodium hydroxide; tetrabutylammomium bromide / 12 h / 0 - 20 °C
3: sodium hydroxide / ethanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: caesium carbonate / acetonitrile / 12 h / 20 °C
2: sodium hydroxide; tetrabutylammomium bromide / chloroform / 12 h / 0 - 20 °C / Autoclave; Large scale
3: sodium hydroxide / ethanol; water / 0.5 h / 20 °C / pH 3 - 4 / Large scale
View Scheme
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium acetate / N,N-dimethyl-formamide / 150 °C
2: caesium carbonate / acetonitrile / 24 h / 20 °C
3: sodium hydroxide; tetrabutylammomium bromide / 12 h / 0 - 20 °C
4: sodium hydroxide / ethanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium acetate / N,N-dimethyl-formamide / 150 °C
2: potassium carbonate / acetonitrile / 48 h / 20 °C
3: trimethyldodecylammonium chloride; sodium hydroxide / 24 h / 20 °C
4: sodium hydroxide / methanol; water / 0.5 h / 20 °C
View Scheme
C13H16O3

C13H16O3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; tetrabutylammomium bromide / 12 h / 0 - 20 °C
2: sodium hydroxide / ethanol / 0.5 h / 20 °C
View Scheme
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethylenediamine / N,N-dimethyl-formamide / 6 h / 150 °C / Large scale
2: caesium carbonate / acetonitrile / 12 h / 20 °C
3: sodium hydroxide; tetrabutylammomium bromide / chloroform / 12 h / 0 - 20 °C / Autoclave; Large scale
4: sodium hydroxide / ethanol; water / 0.5 h / 20 °C / pH 3 - 4 / Large scale
View Scheme
Multi-step reaction with 3 steps
1: diethylamine / toluene / 2 h / 150 °C / Green chemistry
2: sodium hydroxide; tetrabutylammomium bromide / 40 °C / Green chemistry
3: magnesium; titanium tetrachloride / dichloromethane; tetrahydrofuran / 2 h / 0 - 120 °C / Green chemistry
View Scheme
tetrachloromethane
56-23-5

tetrachloromethane

2-methyl-2-(4-vinylphenoxy)propionic acid

2-methyl-2-(4-vinylphenoxy)propionic acid

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
With titanium tetrachloride; magnesium In tetrahydrofuran; dichloromethane at 0 - 120℃; for 2h; Green chemistry;98.6 %Chromat.
bromoethyl isobutyrate
84443-44-7

bromoethyl isobutyrate

4-(2,2-dichlorocyclopropyl)phenyl acetate

4-(2,2-dichlorocyclopropyl)phenyl acetate

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Conditions
ConditionsYield
Stage #1: 4-(2,2-dichlorocyclopropyl)phenyl acetate With potassium carbonate In methanol at 20℃; for 10h;
Stage #2: bromoethyl isobutyrate In methanol for 24h; Reflux;
Stage #3: With water Temperature; Alkaline conditions;
240 g
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

(2S)-2-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)-3-phenylpropansaeure-methylester

(2S)-2-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)-3-phenylpropansaeure-methylester

B

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;A 95%
B n/a
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

ethyl (R)-2-((mesitylsulfinyl)imino)acetate

ethyl (R)-2-((mesitylsulfinyl)imino)acetate

C25H31Cl2NO4S

C25H31Cl2NO4S

Conditions
ConditionsYield
With 9-mesityl-2,7-dimethyl-10-phenylacridin-10-ium tetrafluoroborate; potassium carbonate at 20℃; Inert atmosphere; Irradiation; diastereoselective reaction;91%
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}glycin-methylester

N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}glycin-methylester

B

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;A 87.5%
B n/a
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

methyl 3-aminopropanoate hydrochloride
3196-73-4

methyl 3-aminopropanoate hydrochloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

3-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)propansaeure-methylester

3-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)propansaeure-methylester

B

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;A 84.2%
B n/a
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

methyl γ-aminobutyrate hydrochloride
13031-60-2

methyl γ-aminobutyrate hydrochloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

4-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)butansaeure-methylester

4-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)butansaeure-methylester

B

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;A 83.4%
B n/a
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

L-glutamic dimethyl ester hydrochloride
23150-65-4

L-glutamic dimethyl ester hydrochloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}-L-glutaminsaeure-dimethylester

N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}-L-glutaminsaeure-dimethylester

B

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

N-Cyclohexyl-N-(cyclohexylcarbamoyl)-2-[4-(2,2-dichlorcyclopropyl)phenoxy]-2-methylpropanamid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;A 80%
B n/a
methanol
67-56-1

methanol

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate
130232-51-8, 130233-23-7, 130233-24-8

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With tert.-butylnitrite at 40℃; for 48h;79%
With tert.-butylnitrite at 40℃; for 48h; Green chemistry;79%
Benzophenone oxime
574-66-3

Benzophenone oxime

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

diphenylmethanone O-(2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoyl)oxime

diphenylmethanone O-(2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoyl)oxime

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;78%
4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

(p-tolylthio)methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate

(p-tolylthio)methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In methanol; acetonitrile at 20℃; for 6h; Inert atmosphere; Electrochemical reaction;66%
4-nitro-phenol
100-02-7

4-nitro-phenol

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropansaeure-(4-nitrophenyl)-ester

2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropansaeure-(4-nitrophenyl)-ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h;59.9%
Hexafluorobenzene
392-56-3

Hexafluorobenzene

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

C18H13Cl2F5O

C18H13Cl2F5O

Conditions
ConditionsYield
With Ir(dFFppy)2(dtbbpy)PF6; lithium carbonate In dimethyl sulfoxide at 35℃; for 48h; Inert atmosphere; Irradiation; Sealed tube;54%
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

A

2-(p-acetylphenoxy)-2-methylpropionic acid
52179-07-4

2-(p-acetylphenoxy)-2-methylpropionic acid

B

2-(4-ethynylphenoxy)-2-methylpropanoic acid

2-(4-ethynylphenoxy)-2-methylpropanoic acid

C

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

D

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 56h; Heating; Further byproducts given;A n/a
B 7%
C 42%
D 4%
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

A

4-(1-carboxy-1-methyl-ethoxy)-benzoic acid
42019-57-8

4-(1-carboxy-1-methyl-ethoxy)-benzoic acid

B

2-(4-ethynylphenoxy)-2-methylpropanoic acid

2-(4-ethynylphenoxy)-2-methylpropanoic acid

C

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

D

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 56h; Heating; Further byproducts given;A n/a
B 7%
C 42%
D 4%
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

A

2-(4-ethynylphenoxy)-2-methylpropanoic acid

2-(4-ethynylphenoxy)-2-methylpropanoic acid

B

2-(4-formylphenoxy)-2-methylpropanoic acid
85212-83-5

2-(4-formylphenoxy)-2-methylpropanoic acid

C

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

D

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 56h; Heating; Further byproducts given;A 7%
B n/a
C 42%
D 4%
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

A

2-(p-acetylphenoxy)-2-methylpropionic acid
52179-07-4

2-(p-acetylphenoxy)-2-methylpropionic acid

B

4-(1-carboxy-1-methyl-ethoxy)-benzoic acid
42019-57-8

4-(1-carboxy-1-methyl-ethoxy)-benzoic acid

C

2-(4-ethynylphenoxy)-2-methylpropanoic acid

2-(4-ethynylphenoxy)-2-methylpropanoic acid

D

2-(4-formylphenoxy)-2-methylpropanoic acid
85212-83-5

2-(4-formylphenoxy)-2-methylpropanoic acid

E

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

2-<4-(3-hydroxypropynyl)phenoxy>-2-methylpropanoic acid

F

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

2-<4-(2-carboxyethyl)phenoxy>-2-methylpropanoic acid

G

2-<4-(2-chloro-1-hydroxyprop-2-enyl)- and (2-chloro-3-hydroxyprop-1-enyl)phenoxy>-2-methylpropanoic acid

2-<4-(2-chloro-1-hydroxyprop-2-enyl)- and (2-chloro-3-hydroxyprop-1-enyl)phenoxy>-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 56h; Mechanism; Heating;A n/a
B n/a
C 7%
D n/a
E 42%
F 4%
G n/a
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

A

(Z)-2-<4-(2-chloro-3-hydroxyprop-1-enyl)phenoxy>-2-methylpropanoic acid

(Z)-2-<4-(2-chloro-3-hydroxyprop-1-enyl)phenoxy>-2-methylpropanoic acid

B

2-<4-(2-chloro-1-hydroxyprop-2-enyl)phenoxy>2-methylpropanoic acid

2-<4-(2-chloro-1-hydroxyprop-2-enyl)phenoxy>2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 96h; Heating; pH 7;
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

(+)-2-<4-(2,2-dichlorocyclopropyl)phenoxy>-2-methylpropanoic acid

(+)-2-<4-(2,2-dichlorocyclopropyl)phenoxy>-2-methylpropanoic acid

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

(-)-2-<4-(2,2-dichlorocyclopropyl)phenoxy>-2-methylpropanoic acid

(-)-2-<4-(2,2-dichlorocyclopropyl)phenoxy>-2-methylpropanoic acid

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}glycin
640772-36-7

N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}glycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87.5 percent / Et3N; DMAP / CH2Cl2 / 20 h / 20 °C
2: 94.9 percent / NaOH / methanol; H2O / 4 h / 20 °C
View Scheme
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

3-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)propansaeure

3-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)propansaeure

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84.2 percent / Et3N; DMAP / CH2Cl2 / 20 h / 20 °C
2: 95 percent / NaOH / methanol; H2O / 4 h / 20 °C
View Scheme
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

2-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)ethansulfonsaeure

2-({2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}amino)ethansulfonsaeure

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 59.9 percent / DCC; DMAP / CH2Cl2 / 20 h / 20 °C
2: 27.9 percent / pyridine / H2O / 24 h / 20 °C
View Scheme
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

sulfuric acid
7664-93-9

sulfuric acid

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate
130232-51-8, 130233-23-7, 130233-24-8

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
In methanol; diethyl ether
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

2-amino-1-(4-hydroxyphenyl)ethyl ketone
77369-38-1

2-amino-1-(4-hydroxyphenyl)ethyl ketone

2-(4-(2,2-dichlorocyclopropyl)phenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methylpropanamide
1416548-75-8

2-(4-(2,2-dichlorocyclopropyl)phenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methylpropanamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;760 mg
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

2-amino-1-(4-hydroxyphenyl)ethyl ketone
77369-38-1

2-amino-1-(4-hydroxyphenyl)ethyl ketone

C34H33Cl4NO6
1416548-76-9

C34H33Cl4NO6

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;1.15 g
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

2-(4-hydroxyphenyl)acetamide
17194-82-0

2-(4-hydroxyphenyl)acetamide

2-(4-(2,2-dichlorocyclopropyl)phenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methylpropanamide
1416548-75-8

2-(4-(2,2-dichlorocyclopropyl)phenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methylpropanamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;760 mg
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
52214-84-3

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

2-(4-hydroxyphenyl)acetamide
17194-82-0

2-(4-hydroxyphenyl)acetamide

C34H33Cl4NO6
1416548-76-9

C34H33Cl4NO6

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;1.15 g

52214-84-3Relevant articles and documents

Cyclopropanecarboxylic bethe synthetic method

-

Paragraph 0014, (2018/04/01)

The invention relates to a synthesis method of ciprofibrate. In the synthesis method, acetic acid-4-(2,2-dichlorocyclopropyl) phenyl ester is adopted as a raw material, and 2-[4-(2,2-dichlorocyclopropyl) phenoxy]-2-methylpropanoic acid is obtained through alcoholysis, alkylation and alkaline hydrolysis processes. The synthesis method of ciprofibrate, provided by the invention, has the benefits that the raw materials used in the whole reaction are inexpensive and easy to get, the reaction conditions are mild, the operation is convenient, the yield is good, all solvents used in the reaction can be recycled, and the environmental pollution degree is low.

Synthetic method of lipid-lowering drug ciprofibrate

-

Paragraph 0022; 0054; 0055; 0056; 0063; 0071; 0079, (2017/09/01)

The invention provides a synthetic method of lipid-lowering drug ciprofibrate. The synthetic method comprises the following steps: catalyzing reaction of p-hydroxy benzaldehyde and propane diacid in a mixed solvent by virtue of alkali, so as to generate p-hydroxystyrene; catalyzing reaction of p-hydroxystyrene, acetone, chloroform and alkali by virtue of a phase transfer catalyst, so as to generate an intermediate 2-methyl-2-(4-vinylphenoxy)propionic acid; and reacting 2-methyl-2-(4-vinylphenoxy)propionic acid with TiCl4, Mg and CCl4, so as to generate ciprofibrate. The synthetic method has the beneficial effects that the reaction route is short, the raw materials are cheap and easily available, reaction conditions are mild, the energy consumption is reduced, and the production cost is lowered; the post-processing step is simple, the emission of three wastes is reduced, and the method is environment-friendly and safe. Compared with routes of predecessors, the synthetic method has the advantages that the reaction selectivity and conversion rate of the route are relatively high, the wasting of the raw materials is reduced, and the economical efficiency is relatively high.

A method for preparing the fat cumaric acupoint of the c bethe method

-

, (2017/10/07)

The invention discloses a method for preparing a hypolipidemic medicine ciprofibrate with p-coumaric acid. The method comprises the following specific steps: p-coumaric acid (I) is subjected to a decarboxylation reaction under the effect of an alkaline catalyst, such that p-hydroxystyrene (II) is obtained; p-hydroxystyrene (II) is subjected to a reaction with 2-haloisobutyrate under the effect of alkali, such that an etherified product (III) is obtained; under an alkaline condition, the etherified product (III) and chloroform are subjected to a cyclization reaction under the effect of a phase transfer catalyst, such that a cyclized product (IV) is obtained; the cyclized product (IV) is subjected to alcoholysis and acidification in an alkali solution; and recrystallization is carried out, such that ciprofibrate (V) is obtained. The method provided by the invention has the advantages of short synthesis process, safe operation and easy post-treatment. The method is suitable for large-scale industrialized productions, and almost has no possibility of causing accidents such as explosion. During the entire reaction process, only conventional acid, alkali and solvent are used, such that the cost is low. The solvent can be recovered and reused, such that the method is environment-friendly. With the method, the yield is improved by more than 20%.

A new method for synthesizing cyclopropanecarboxylic Bethe

-

, (2018/02/04)

The invention discloses a novel ciprofibrate synthesis method. The novel ciprofibrate synthesis method comprises the specific steps that p-hydroxy benzaldehyde (I) and malonic acid perform condensation decarboxylation reaction in the presence of an alkaline catalyst to obtain p-hydroxystyrene (II), the p-hydroxystyrene (II) reacts with 2-halogenated isobutyrate under the action of alkali to obtain an etherification product (III), the etherification product (III) and chloroform perform cyclization reaction under the alkaline condition and under the action of a phase transfer catalyst to obtain a cyclization product (IV), and the cyclization product (IV) is subjected to alcoholysis, acidification and recrystallization in an alkaline solution to obtain ciprofibrate (V). The novel ciprofibrate synthesis method comprises few synthesis steps, industrial operation is simple and convenient, the conditions are moderate and are easy to control, almost no possibility of explosion and other accidents exists, operation is safe, aftertreatment is convenient, a process is stable, large-scale industrial production is easy to achieve, only conventional acid, alkali and solvents are used in the whole reaction process, the novel ciprofibrate synthesis method is low in cost and is environmentally friendly, and the yield is improved by above 15%.

Treatment of skin conditions by use of PPAR alpha activators

-

, (2008/06/13)

Disorders of the skin and mucous membrane that have a disrupted or dysfunctional epidermal barrier are treated or prevented by topical application of compounds that are either activators of the farnesoid X receptor, activators of the peroxisome proliferator-activated receptor alpha , and oxysterol activators of the LXR alpha receptor. The same compounds are also effective in treating disorders of epidermal differentiation and proliferation.

FXR, PPARA and LXRA activators to treat acne/acneiform conditions

-

, (2008/06/13)

Acne vulgaris and acneiform skin conditions are treated by the application of compounds that is juvenile hormone III, 7-methyl-9-(3,3-dimethyloxiranyl)-3-methyl-2,6-nonadienoic acid methyl ester.

Levo-ciprofibrate

-

, (2008/06/13)

Levo-ciprofibrate or a pharmaceutically acceptable salt thereof is disclosed.

Dextro-ciprofibrate

-

, (2008/06/13)

Dextro-ciprofibrate or a pharmaceutically acceptable salt thereof is disclosed.

Method for the preparation of fibrates

-

, (2008/06/13)

The present invention relates to a method for the preparation of fibrates of the formula I according to the mechanism: STR1 in which R1 represents especially a halogen atom (in particular F, Cl or Br, the preferred halogen atom being Cl) or an acetyl, (4-chlorophenyl)hydroxymethyl, 4-chlorobenzoyl or 2-(4-chlorobenzamido)ethyl group and R2 represents a C1 -C4 alkyl group in which the hydrocarbon chain is linear or branched, the reaction V+VI being carried out without a solvent.

Halocyclopropyl substituted phenoxyalkanoic acids

-

, (2008/06/13)

Halocyclopropyl substituted phenoxyalkanoic acids and esters thereof, having hypocholesteremic activity are prepared via several alternative synthetic approaches, involving as the key reactions interaction of a substituted phenylalkene with a carbene source to introduce the halocyclopropyl moiety, and reaction of a substituted phenol with chloroform and a lower-alkanone in the presence of base, or with a lower-alkyl α-bromo-alkanoate, to form the phenoxyalkanoic acid moiety.

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