2-(4-Chlorophenoxy)-2-methylpropionic acid Chemical Properties

Melting point:

120-122 °C(lit.)

Boiling point:

308.11°C (rough estimate)

Density 

1.2413 (rough estimate)

refractive index 

1.5220 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Crystals or Crystalline Powder

pka

3.18±0.10(Predicted)

color 

Pale yellow to brownish

Merck 

14,2378

BRN 

1874067

CAS DataBase Reference

882-09-7(CAS DataBase Reference)

NIST Chemistry Reference

Clofibric acid(882-09-7)

EPA Substance Registry System

Propanoic acid, 2-(4-chlorophenoxy)-2-methyl- (882-09-7)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-20/21/22

Safety Statements 

36-24/25

WGK Germany 

3

RTECS 

UE9455000

HazardClass 

IRRITANT

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-(4-Chlorophenoxy)-2-methylpropionic acid Usage And Synthesis

Description

Clofibric acid is a peroxisome proliferator-activated receptor α (PPARα) agonist (EC₅₀ = 50 μM in a transactivation assay) and the active metabolite of clofibrate . It is formed from clofibrate by tissue and serum esterases. Dietary administration of clofibric acid (0.067-0.22%) reduces serum cholesterol, phospholipid, and triglyceride levels in rats. It decreases glutamate oxaloacetate transaminase (GOT) levels and increases glutamate pyruvate transaminase (GPT) and lactate dehydrogenase (LDH) levels, markers of xenobiotic stress, in the plasma of carp (C. carpio) when administered in tank water at a concentration of 10 μg/L. Clofibric acid has been found in wastewater effluent.

Chemical Properties

Pale Yellow Solid

Uses

Antilipemic.

Uses

herbicide, antihyperlipoproteinemic, antineoplastic

Uses

A hypolipidemic compound

Definition

ChEBI: A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.

Biological Activity

PPAR agonist. Antihyperlipoproteinemic.

Synthesis

Step 2: Synthesis of 2-(4-chlorophenoxy)-2-methylpropionic acid To a solution of ethyl 2-(4-chlorophenoxy)-2-methylpropionate (2.0 g, 8.24 mmol) in tetrahydrofuran (16 mL) was added sequentially water (4 mL) and lithium hydroxide monohydrate (0.69 g, 16.4 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was diluted with water and washed with dichloromethane (DCM). The aqueous phase was separated and acidified with 1 M aqueous hydrochloric acid to pH about 2, followed by extraction with dichloromethane (DCM, 2 times). The organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 2-(4-chlorophenoxy)-2-methylpropionic acid (p-chlorophenoxyisobutyric acid) as a white solid (1.45 g, 82% yield). 1H NMR (400 MHz, chloroform-d): δ 1.62 (6H, s), 6.89 (2H, d, J = 9.0 Hz), 7.24 (2H, d, J = 9.0 Hz).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 681 - 694
[2] Patent: WO2009/105509, 2009, A1. Location in patent: Page/Page column 36-37
[3] Journal of Pharmaceutical Sciences, 1980, vol. 69, # 1, p. 92 - 93
[4] Patent: WO2008/104994, 2008, A2. Location in patent: Page/Page column 32-33
[5] Patent: US2009/197959, 2009, A1. Location in patent: Page/Page column 18

2-(4-Chlorophenoxy)-2-methylpropionic acid(882-09-7)Related Product Information

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• OCTYL ISOBUTYRATE
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• Diethoxydimethylsilane
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• Citric acid
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• Ascoric Acid