2-FLUORO-5-(TRIFLUOROMETHYL)BENZOIC ACID Chemical Properties

Melting point:

100-103 °C (lit.)

Boiling point:

236℃

Density 

1.489

Flash point:

96℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly),

pka

2.84±0.10(Predicted)

form 

Solid

color 

Off-White to Pale Beige

BRN 

5813056

InChI

InChI=1S/C8H4F4O2/c9-6-2-1-4(8(10,11)12)3-5(6)7(13)14/h1-3H,(H,13,14)

InChIKey

LIFKXWNFWIUMJT-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(C(F)(F)F)=CC=C1F

CAS DataBase Reference

115029-23-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

2-FLUORO-5-(TRIFLUOROMETHYL)BENZOIC ACID Usage And Synthesis

Chemical Properties

White to off-white powder

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 7495, 1992 DOI: 10.1016/S0040-4039(00)60805-5

Synthesis

General procedure for the synthesis of 2-fluoro-5-trifluoromethylbenzoic acid from 4-fluorobenzotrifluoride: 99 g (0.6 mol) of 4-fluorobenzotrifluoride was dissolved in 750 ml of tetrahydrofuran at -60 °C and protected by nitrogen, and 256 ml (0.64 mol) of a 2.5 M butyl lithium hexane solution was added slowly dropwise over a controlled period of time. The reaction mixture was stirred continuously at -60 °C to -70 °C for 4 h and subsequently poured into a large excess of dry ice. after 15 min, the excess dry ice was evaporated by external heating and the solvent was removed by rotary evaporator. The residue was dissolved in 500 ml of water, 30 ml of 1N sodium hydroxide solution was added and washed with 2 x 300 ml of ethyl acetate. The aqueous phase was acidified with concentrated hydrochloric acid and then extracted with 2 x 300 ml ethyl acetate. The organic phases were combined and washed sequentially with 500 ml of water and 300 ml of saturated saline, dried over anhydrous sodium sulfate and concentrated by rotary evaporation. The crude product was recrystallized by hexane to give 80 g of white analytically pure crystals with 64% yield and melting point of 205°C. The product was extracted with 500 ml of water and 300 ml of saturated saline. Elemental analysis results (C8H4O2F4): calculated value C 46.17%, H 1.94%; measured value C 46.16%, H 1.89%.

References

[1] Patent: US4705853, 1987, A
[2] Patent: US5304532, 1994, A

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