2-Bromo-6-chlorobenzoic acid

2-Bromo-6-chlorobenzoic acid Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2-Bromo-6-chlorobenzoic acid Chemical Properties,Usage,Production

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