2-Bromo-3-methylbenzoic acid Chemical Properties

Melting point:

135-138 °C (lit.)

Boiling point:

308.3±30.0 °C(Predicted)

Density 

1.599±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Powder

pka

2.92±0.10(Predicted)

color 

Off-white

CAS DataBase Reference

53663-39-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich

2-Bromo-3-methylbenzoic acid Usage And Synthesis

Chemical Properties

Off-white powder

Uses

2-Bromo-3-methylbenzoic acid may be used to synthesize N-phenyl-3-methylanthranilic acid via copper-catalyzed amination reaction with aniline.

General Description

2-Bromo-4-nitrotoluene is formed as an intermediate during the synthesis of 2-bromo-3-methylbenzoic acid. 2-Bromo-3-methylbenzoic acid can be obtained from 2-bromo-4-nitrotoluene via Von-Richter reaction.

Synthesis

The general procedure for synthesizing 2-bromo-3-methylbenzoic acid from 2-amino-3-methylbenzoic acid was as follows: referring to Example 1 (0142), 1.00 g of 2-amino-3-methylbenzoic acid, 8 mL of acetic acid, 4 mL of 50% hydrobromic acid, and 16 mL of water were mixed, followed by the addition of 0.46 g of sodium nitrite and 3 mL of water chilled on ice. After stirring the mixture in an ice bath for 10 minutes, the complete reaction of 2-amino-3-methylbenzoic acid was confirmed by silica gel thin layer chromatography (Spreader: hexane/ethyl acetate = 1/1, Rf value of 0.67 for 2-amino-3-methylbenzoic acid). Next, 1.42 g of copper bromide and 5 mL of water were added and the mixture was heated and reacted at 50 °C for 3 hours. Upon completion of the reaction, water was added to the mixture and the precipitate was collected by filtration to give 1.0 g of 2-bromo-3-methylbenzoic acid. (0143) 1H-NMR (CDCl3) δ (ppm): 2.49 (3H, s), 7.29 (1H, t, J=7.6Hz), 7.42 (1H, d, J=7.2Hz), 7.70 (1H, t, J=3.9Hz).

References

[1] Patent: US2017/57935, 2017, A1. Location in patent: Paragraph 0142; 0143

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