4-Bromo-3-fluorobenzoic acid Chemical Properties

Melting point:

207 °C

Boiling point:

296.1±25.0 °C(Predicted)

Density 

1.789±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder

pka

3.63±0.10(Predicted)

color 

Off white to cream

InChI

InChI=1S/C7H4BrFO2/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3H,(H,10,11)

InChIKey

RMYOGXPGIDWJLU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

153556-42-4(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 4-bromo-3-fluoro- (153556-42-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2916399090

MSDS

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4-Bromo-3-fluorobenzoic acid Usage And Synthesis

Chemical Properties

White solid powder

Uses

4-Bromo-3-fluorobenzoic acid is an important chemical raw material and can be used to prepare a variety of drugs (such as the anticancer drug benzamide).

Synthesis

The general procedure for the synthesis of 3-fluoro-4-bromobenzoic acid from 3-fluoro-4-bromotoluene was as follows: potassium permanganate (66.0 g, 0.42 mol) was added to a mixed solution of pyridine and water (1:1 ratio, 200 mL) containing 1-bromo-2-fluoro-4-methylbenzene (20.0 g, 0.10 mol) in batches. The reaction mixture was stirred at 90 °C for 3 hours. After completion of the reaction, it was cooled to room temperature and filtered through a diatomaceous earth pad. The diatomaceous earth pad was washed sequentially with 3N sodium hydroxide solution (500 mL) and water (400 mL). Subsequently, ethanol was removed by distillation under reduced pressure and the residue was acidified to pH=2 with 6N hydrochloric acid to produce a white precipitate. The precipitate was filtered and dried to give 4-bromo-3-fluorobenzoic acid as a white solid (17.0 g, 73% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[3] Patent: WO2011/21209, 2011, A1. Location in patent: Page/Page column 38
[4] Patent: US2012/101099, 2012, A1. Location in patent: Page/Page column 13; 14
[5] Patent: WO2006/64251, 2006, A1. Location in patent: Page/Page column 80

4-Bromo-3-fluorobenzoic acid(153556-42-4)Related Product Information

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