2-Bromo-6-chlorobenzoic acid Chemical Properties

Melting point:

148-152 °C

Boiling point:

315.9±27.0 °C(Predicted)

Density 

1.809±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

powder to crystal

pka

1.62±0.10(Predicted)

color 

White to Orange to Green

InChIKey

URGXUQODOUMRFP-UHFFFAOYSA-N

CAS DataBase Reference

93224-85-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-36/37/38

Safety Statements 

26-45

RIDADR 

2811

WGK Germany 

2

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2916399090

2-Bromo-6-chlorobenzoic acid Usage And Synthesis

Chemical Properties

off-white powder

Uses

2-Bromo-6-chlorobenzoic acid is used in the syntheis of Diclofenac Monobromo Sodium Salt Impurity (D436490).

Synthesis

Step 1. Synthesis of 2-bromo-6-chlorobenzoic acid: Diisopropylamine (3.5 mL, 25 mmol) was slowly added to a tetrahydrofuran (THF, 70 mL) solution of n-butyllithium (n-BuLi, 10 mL, 25 mmol, 2.5 M hexane solution) cooled at -78 °C under anhydrous conditions. After stirring the reaction mixture for 15 minutes, 1-chloro-3-bromobenzene (4.32 g, 25 mmol) was added dropwise and stirring was continued at -78 °C for 2 hours. Subsequently, dry ice (solid CO2) was added to the reaction system and after 15 min of reaction, aqueous 2N hydrochloric acid (100 mL) was slowly added to quench the reaction. The reaction mixture was extracted with ethyl acetate (EtOAc) and the organic phases were combined. The product was purified by recrystallization from hexane and finally isolated to give 5 g of 2-bromo-6-chlorobenzoic acid in 85% yield.

References

[1] Organic Letters, 2009, vol. 11, # 5, p. 1051 - 1054
[2] Tetrahedron Letters, 1997, vol. 38, # 9, p. 1559 - 1562
[3] Patent: WO2008/124582, 2008, A1. Location in patent: Page/Page column 117
[4] Patent: WO2008/124575, 2008, A1. Location in patent: Page/Page column 108
[5] Organic Process Research and Development, 2005, vol. 9, # 6, p. 764 - 767

2-Bromo-6-chlorobenzoic acid(93224-85-2)Related Product Information

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