ChemicalBook--->CAS DataBase List--->195457-70-6

195457-70-6

195457-70-6 Structure

195457-70-6 Structure
IdentificationMore
[Name]

3'-TRIFLUOROMETHYLBIPHENYL-4-CARBOXYLIC ACID
[CAS]

195457-70-6
[Synonyms]

AKOS BAR-0024
RARECHEM AL BE 1367
4-[3-(trifluoromethyl)phenyl]benzoate
4-(3-(Trifluoromethyl)phenyl)benzoic acid
3'-TRIFLUOROMETHYLBIPHENYL-4-CARBOXYLIC ACID
3'-(TRIFLUOROMETHYL)-1,1'-BIPHENYL-4-CARBOXYLIC ACID
[1,1'-BIPHENYL]-4-CARBOXYLIC ACID, 3'-(TRIFLUOROMETHYL)-
[Molecular Formula]

C14H9F3O2
[MDL Number]

MFCD03424607
[Molecular Weight]

266.22
[MOL File]

195457-70-6.mol
Chemical PropertiesBack Directory
[storage temp. ]

Sealed in dry,Room Temperature
[form ]

solid
[color ]

Yellow
[CAS DataBase Reference]

195457-70-6(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

Xi
[Hazard Note ]

Irritant
[HS Code ]

2916399090
Hazard InformationBack Directory
[Uses]

4-(3-Trifluoromethylphenyl)benzoic Acid is a reagent used in the synthesis of aryl-substituted aspartic acid and diaminopropionic acid derivatives as inhibitors of glutamate transporter EAAT-2 (Excitatory amino acid transporters 2).
[Synthesis]

4-Bromobenzoic acid

586-76-5

3-(Trifluoromethyl)phenylboronic acid

1423-26-3

3'-TRIFLUOROMETHYLBIPHENYL-4-CARBOXYLIC ACID

195457-70-6

The general procedure for the synthesis of 4-(3-trifluoromethylphenyl)benzoic acid from 4-bromobenzoic acid and 3-(trifluoromethyl)phenylboronic acid was as follows: Pd(dppf)Cl2 (1.49 mmol, 1.09 g) was added to a mixture containing 4-bromobenzoic acid (14.9 mmol, 3.0 g), 3-(trifluoromethyl)phenylboronic acid (17.9 mmol, 3.4 g), and Cs2CO3 (37.3 mmol, 12.2 g) in a suspension with the solvent being a mixture of 30 mL dioxane and 7.5 mL ethanol. The reaction mixture was stirred at 80 °C for 2 hours. After completion of the reaction, it was cooled to room temperature, the solid product was collected by filtration and washed with methanol. The filtrate was concentrated and the residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To the concentrated residue was added dichloromethane, the resulting solid was collected by filtration, washed with dichloromethane and dried to give 4-(3-trifluoromethylphenyl)benzoic acid (3.58 g, 86% yield), which could be used in the next reaction without further purification.

[References]

[1] Patent: US2013/102584, 2013, A1. Location in patent: Paragraph 0307; 0308
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3144 - 3150
Spectrum DetailBack Directory
[Spectrum Detail]

3'-TRIFLUOROMETHYLBIPHENYL-4-CARBOXYLIC ACID(195457-70-6)1HNMR
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