2-Bromo-5-fluorobenzoic acid Chemical Properties

Melting point:

154-157 °C (lit.)

Boiling point:

291.1±25.0 °C(Predicted)

Density 

1.789±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.51±0.10(Predicted)

color 

White to Almost white

BRN 

2575978

InChI

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

InChIKey

OQBMJMJZMDBQSM-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(F)=CC=C1Br

CAS DataBase Reference

394-28-5(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 2-bromo-5-fluoro- (394-28-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

2-Bromo-5-fluorobenzoic acid Usage And Synthesis

Uses

2-Bromo-5-fluorobenzoic acid, a common organic synthesis intermediate, is primarily used to synthesize target molecular structures by utilizing the bromine and fluorine atoms on the benzene ring. For example, the bromine atom can undergo Suzuki coupling to introduce an aromatic ring or alkyl chain; or it can be converted into boric acid or borate esters, leveraging the versatility of borate esters to synthesize complex molecules. The fluorine atom can also undergo a series of transformations, including aromatic nucleophilic substitution reactions. Finally, the carboxyl group on the benzene ring can be readily converted into amides, esters, viboramides, etc.

Chemical Properties

white to light yellow crystal powder

Synthesis

2-Bromo-5-fluorobenzoic acid is synthesized from 5-(2′-bromophenoxy)benzothiazole and 2,3,4,5,6-pentafluorobenzoyl chloride in three steps. The synthesis involves bromination of benzothiazole with NBS followed by reaction with 4-fluoroaniline to give the intermediate which is then reacted with pentafluorobenzoyl chloride.

References

[1] Patent: WO2005/56544, 2005, A1. Location in patent: Page/Page column 46

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