4-(Trifluoromethyl)-2'-biphenylcarboxylic acid Chemical Properties

Melting point:

169-171 °C(lit.)

Boiling point:

335.8±37.0 °C(Predicted)

Density 

1.326±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.70±0.36(Predicted)

color 

White to Almost white

BRN 

7577560

CAS DataBase Reference

84392-17-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29162090

MSDS

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

4-(Trifluoromethyl)-2'-biphenylcarboxylic acid Usage And Synthesis

Chemical Properties

White solid

Originator

Xenalipin ,Wellcome (GSK)

Uses

Hypolipidemic.

Uses

4''-(Trifluoromethyl)-2-biphenylcarboxylic Acid, is a novel compound which has been found to be effective hypolipidemic agent in animal species. It is also an intermediate in the synthesis of various pharmaceutical compounds, such as Cannabinol (C175350).

Manufacturing Process

a). Preparation of 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-trifluoromethylbiphenyl:
A mechanically stirred solution of magnesium turnings (5.1 g, 0.21 mole) Mallinckrodt, for Grignards reaction, and 2-(2-methoxyphenyl)-4,4-dimethyl- 2-oxazoline (41 g, 0.2 mole) in 50 mL dry tetrahydrofuran under nitrogen was prepared. To this was added a crystal of iodine, 1 mL of dibromethane and 2 mL of neat p-bromotrifluoromethylbenzene to initiate the Grignard reaction. Following initiation of the reaction, the remainder of the p- bromotrifluoromethylbenzene (50 g, 0.22 mole total) in 100mL dry tetrahydrofuran was added dropwise at a rate sufficient to maintain the reaction at gentle reflux. The addition took 1 hour. At the end of the addition period, the reaction mixture was heated to reflux for 3 hours. The reaction mixture was then cooled to room temperature and 10 mL water was added dropwise to coagulate the salts. The tetrahydrofuran was decanted and the remaining solids were slurried twice with 300 mL ethyl ether and twice with 300 mL dichloromethane. Each organic extract was decanted from the solids in turn and combined and evaporated under reduced pressure to an oil.
This oil was redissolved in 300 mL dichloromethane, washed once with 100 mL water and once with 10 mL saturated sodium chloride solution, dried and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (0.040 mm, 95.degree.) to yield 2-(4,4-dimethyl-2- oxazoline-2-yl)-4'-trifluoromethylbiphenyl, yield 33%. A sample was recrystallized from 30-60°C petroleum ether (melting point 50-51°C).
b). Preparation of 4'-(trifluoromethyl)-2-biphenylcarboxylic acid:
A solution of 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-trifluoromethylbiphenyl (3.5 g, 0.011 mole) in 60 mL 6 N hydrochloric acid was stirred at vigorous reflux for 2 hr. The reaction mixture was then cooled to room temperature and extracted with methylene chloride. The organic extracts were dried and concentrated under reduced pressure to yield a solid. Recrystallisation from ethyl ether/pentane afforded 4'-(trifluoromethyl)-2-biphenyl carboxylic acid, yield 86% (melting point 167-169°C).

Therapeutic Function

Antihyperlipidemic

General Description

4′-(Trifluoromethyl)-2-biphenylcarboxylic acid (xenalipin) has been tested as an effective hypolipidemic agent in animal species. It has been shown to cause significant reduction in serum cholesterol and triglyceride levels in animal models and would be beneficial in therapy for hyperlipidemia. Synthesis of 4′-(trifluoromethyl)-2-biphenylcarboxylic acid (xenalipin) has been reported. Xenalipin has been synthesized in the [¹⁴C]-labelled form, with specific activity 21.0mCi/mmol, which is suitable for the metabolism and distribution studies in animals.

4-(Trifluoromethyl)-2'-biphenylcarboxylic acid(84392-17-6)Related Product Information

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