3-Bromo-5-fluorobenzoic acid Chemical Properties

Melting point:

140 °C

Boiling point:

303.3±27.0 °C(Predicted)

Density 

1.789±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.47±0.10(Predicted)

color 

White to Almost white

Water Solubility 

Insoluble in water.

InChI

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

InChIKey

KLSLJMGWUPAQGZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

176548-70-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39-36/37

HazardClass 

IRRITANT

HS Code 

29163100

3-Bromo-5-fluorobenzoic acid Usage And Synthesis

Chemical Properties

light yellow powder

Uses

3-Bromo-5-fluorobenzoic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Synthesis

The general procedure for the synthesis of 3-bromo-5-fluorobenzoic acid from 3-bromo-5-fluorobenzonitrile was as follows: 3-bromo-5-fluorobenzonitrile (2.8 g, 13.8 mmol) was mixed with 5 M aqueous sodium hydroxide (28 mL) and heated to reflux for 2 hr. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with concentrated hydrochloric acid to 1. Subsequently, the precipitate precipitated was collected by filtration, the solid was washed with cold water and dried to give 3-bromo-5-fluorobenzoic acid (2.8 g, 94% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CD3OD): δ 6.31 (dt, J = 8.08, 2.02 Hz, 1H), 6.37-6.43 (m, 1H), 6.68 (s, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 22, p. 6974 - 6979,6

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