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HomeProduct name list4-(Trifluoromethyl)-2'-biphenylcarboxylic acid

4-(Trifluoromethyl)-2'-biphenylcarboxylic acid

4-(Trifluoromethyl)-2'-biphenylcarboxylic acid Structural

What is 4-(Trifluoromethyl)-2'-biphenylcarboxylic acid?

Chemical properties

White solid

Originator

Xenalipin ,Wellcome (GSK)

The Uses of 4-(Trifluoromethyl)-2'-biphenylcarboxylic acid

Hypolipidemic.

The Uses of 4-(Trifluoromethyl)-2'-biphenylcarboxylic acid

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.

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

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 for 4-(Trifluoromethyl)-2'-biphenylcarboxylic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 4-(Trifluoromethyl)-2'-biphenylcarboxylic acid

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