4-Bromo-2-methylbenzoic acid Chemical Properties

Melting point:

180-184 °C

Boiling point:

310.1±30.0 °C(Predicted)

Density 

1.599±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.63±0.25(Predicted)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Insoluble in water.

BRN 

2249816

InChI

InChI=1S/C8H7BrO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4H,1H3,(H,10,11)

InChIKey

RVCJOGNLYVNRDN-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(Br)C=C1C

CAS DataBase Reference

68837-59-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Bromo-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

White to brown crystal powde

Uses

A building block which is used in preparation of anthranilic acids possessing antibacterial activity. 4-bromo-2-methylbenzoic acid could be used to synthesis 4-chloro-3'-(2-cyclopentyl-1-oxoisoindolin-5-yl)biphenyl-3-carboxylic acid through Suzuki couplings[1].

Synthesis

General procedure for the synthesis of 2-methyl-4-bromobenzoic acid from 4-bromo-2-methylbenzonitrile: 4-bromo-2-methylbenzonitrile (1 mmol) was suspended in water (49 mL) and potassium hydroxide (50 mmol) was added. The reaction mixture was stirred overnight under reflux conditions. Upon completion of the reaction, it was cooled to room temperature and the basic aqueous solution was washed with ethyl acetate (3 x 15 mL) to remove unreacted material. Subsequently, the aqueous phase was acidified to pH < 2 with 6 M hydrochloric acid and the acidified aqueous phase was extracted with ethyl acetate (3 x 15 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the white solid product 2-methyl-4-bromobenzoic acid. Yield: 60%. Thin Layer Chromatography (TLC) analysis (unfolding agent: dichloromethane/methanol = 9:1): Rf = 0.46. melting point: 182 °C. 1H-NMR (300 MHz, CD3OD) δ (ppm): 7.80 (d, J = 8.4 Hz, 1H, H-6), 7.48 (s, 1H, H-3), 7.42 (d, J = 8.4 Hz, 1H, H- 5), 2.56 (s, H- 5), 2.56 (s, H- 5), 2.56 (s, H- 5). 5), 2.56 (s, 3H, CH3).

References

[1] Shyama Sidique. “Orally Active Metabotropic Glutamate Subtype 2 Receptor Positive Allosteric Modulators: Structure–Activity Relationships and Assessment in a Rat Model of Nicotine Dependence.” Journal of Medicinal Chemistry 55 22 (2012): 9434–9445.

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