2-Bromo-3-fluorobenzoic acid Chemical Properties

Melting point:

158-160°C

Boiling point:

292.7±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 Light yellow to Light orange

InChI

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

InChIKey

KQRCBMPPEPNNDS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

132715-69-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39-37

HazardClass 

IRRITANT

HS Code 

29163990

2-Bromo-3-fluorobenzoic acid Usage And Synthesis

Chemical Properties

Off-white powder

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 881, 1995 DOI: 10.1016/0040-4039(94)02385-O

Synthesis

The general procedure for the synthesis of 2-bromo-3-fluorobenzoic acid from 2-amino-3-fluorobenzoic acid is as follows: in a 1L three-necked round-bottomed flask equipped with a dropping funnel and a thermometer, 20g (0.13 mol) of 2-amino-3-fluorobenzoic acid and 160mL of acetonitrile were added. After the mixture was cooled to 0 °C, 160 mL of 47% hydrobromic acid solution was added slowly and dropwise over 10 min. Subsequently, a solution prepared from 10 g (0.145 mol) of sodium nitrite (NaNO2) dissolved in 20 mL of water was added dropwise to the reaction system over 1 hour. After the dropwise addition, the reaction mixture was continued to be stirred at 0°C for 5 min. Next, 21.8 g (0.15 mol) of copper bromide (CuBr) was added in batches over 30 minutes. The reaction mixture was transferred to a 70°C oil bath and stirred continuously for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C, diluted with 700 mL of water and the precipitate was collected by filtration. The precipitate was washed with cold water and dried under vacuum to give the orange solid product 2-bromo-3-fluorobenzoic acid in a yield of 22 g and 78%.

References

[1] Patent: US2008/293708, 2008, A1. Location in patent: Page/Page column 37
[2] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2151 - 2163

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