Methyl 3-bromo-4-methylbenzoate Chemical Properties

Melting point:

38-44 °C(lit.)

Boiling point:

130°C/0.1mmHg(lit.)

Density 

1.433±0.06 g/cm3(Predicted)

refractive index 

1.5570 to 1.5610

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in dimethyl sulfoxide.

form 

clear liquid

color 

Colorless to Light orange to Yellow

InChI

InChI=1S/C9H9BrO2/c1-6-3-4-7(5-8(6)10)9(11)12-2/h3-5H,1-2H3

InChIKey

MASRAGFWFYHMFI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

104901-43-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2916399090

MSDS

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

Methyl 3-bromo-4-methylbenzoate Usage And Synthesis

Chemical Properties

Orange-red solid

Uses

It is a pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 5545, 1988 DOI: 10.1021/jo00258a030

Synthesis

The general procedure for the synthesis of methyl 3-bromo-4-methylbenzoate from methanol and 3-bromo-4-methylbenzoic acid was as follows: 3-bromo-4-methylbenzoic acid (2.0 g, 9.30 mmol) was suspended in methanol (20 ml), and sulfuric acid (0.04 ml) was added as a catalyst. The reaction mixture was stirred at 60°C for 42 hours. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title compound methyl 3-bromo-4-methylbenzoate as an orange oil (2.25 g, quantitative yield), which could be used for subsequent experiments without further purification.

References

[1] Patent: US2013/237537, 2013, A1. Location in patent: Paragraph 0330-0331
[2] Patent: WO2013/119946, 2013, A1. Location in patent: Paragraph 0198; 0345
[3] Patent: WO2011/107608, 2011, A1. Location in patent: Page/Page column 69
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6442 - 6446
[5] Patent: WO2006/4903, 2006, A2. Location in patent: Page/Page column 125

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