5-Bromo-2-chlorobenzoic acid Chemical Properties

Melting point:

154-156 °C (lit.)

Boiling point:

324.5±27.0 °C(Predicted)

Density 

1.7312 (rough estimate)

refractive index 

1.5590 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

2.63g/l

pka

2.49±0.25(Predicted)

form 

Solid

color 

Off white colored powder

Water Solubility 

Soluble in water 2.63 g/L @20°C.

BRN 

2691432

InChI

InChI=1S/C7H4BrClO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11)

InChIKey

FGERXQWKKIVFQG-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Br)=CC=C1Cl

CAS DataBase Reference

21739-92-4(CAS DataBase Reference)

NIST Chemistry Reference

5-Bromo-2-chlorobenzoic acid(21739-92-4)

EPA Substance Registry System

Benzoic acid, 5-bromo-2-chloro- (21739-92-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163900

MSDS

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5-Bromo-2-chlorobenzoic acid Usage And Synthesis

Description

5-Bromo-2-chlorobenzoic acid (BCBA) is an organic reagent that can be used in electroinduced dehalogenation reactions. Ag/Cu electrodes exhibit high electrocatalytic activity in the dehalogenation reaction of BCBA. The process is characterised by a sequence of halide excretion and hydrogen addition. Since the bond dissociation energy value of C-Br bond is smaller than that of C-Cl bond, Br-w is more easily released from the benzene ring. As C-Br breaks, BCBA gains electrons and hydrogen to form the intermediate 2-chlorobenzoate. C-Cl then breaks in the same way to give the final product benzoate.

Chemical Properties

white to light yellow crystal powder

Uses

5-Bromo-2-chlorobenzoic acid was used to evaluate the homogeneity of organic powder. It can be used to produce 2-chloro-5-deuteriobenzoic acid.

Synthesis

4.7g (0.03 mol) of 2-chlorobenzoic acid, 40mL of concentrated sulfuric acid and 0.936g (0.012 mol) of sodium sulfide are sequentially added into a 250mL four-mouth bottle, stirred for 20 minutes at 30 ℃ until the solution is clear, then 5.334g N-bromosuccinimide (0.03 mol) is added, the reaction is continued for 10 minutes at 30 ℃, and then the solution is slowly poured into 80mL ice water bath for crystallization to obtain a crude product of the 5-bromo-2-chlorobenzoic acid. Add the filter cake into a 250mL four-mouth bottle, add 24mL methanol and 36mL water, heat to 60 ℃, naturally cool, and stir for crystallization. Filtration, washing with 20mL of 40% volume fraction aqueous methanol, and drying at 55 ℃ for 6 hours gave 6.001g of a white solid, yield: 85.0%.

References

[1] Fen Wang . “The Electroreductive Dehalogenation Reaction of 5-Bromo-2-chlorobenzoic Acid on Dendritic Ag/Cu.” International Journal of Electrochemical Science 10 6 (2015): Pages 5101-5111.

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