METHYL 4-BROMO-2-METHOXYBENZOATE 98 Chemical Properties

Melting point:

33 °C (lit.)

Boiling point:

100-108 °C/0.01 mmHg (lit.)

Density 

1.462±0.06 g/cm3(Predicted)

refractive index 

1.58

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

low-melting solid

color 

White to Light yellow

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29189900

METHYL 4-BROMO-2-METHOXYBENZOATE 98 Usage And Synthesis

Chemical Properties

White powder

Uses

Methyl 4-bromo-2-methoxybenzoate is an organic compound, commonly used as an intermediate for medicines and pesticides, and also a raw material for organic synthesis.

Synthesis

The general procedure for the synthesis of methyl 4-bromo-2-methoxybenzoate from 2-hydroxy-4-bromobenzoic acid and iodomethane was as follows: 4-bromo-2-hydroxybenzoic acid (1.00 g, 4.61 mmol) was dissolved in acetone (25 mL), followed by the addition of iodomethane (1.15 mL, 18.4 mmol) and potassium carbonate (2.55 g, 18.4 mmol). The reaction mixture was heated to reflux and the reaction was continued overnight. After completion of the reaction, it was cooled to room temperature, filtered to remove insoluble material, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography (Biotage column, eluent: 10% ethyl acetate/hexane) to give 0.955 g (85% yield) of the target compound, methyl 4-bromo-2-methoxybenzoate, as a yellow oil. The product was analyzed by LC/MS showing a m/z of 245.0 (MH+) and a retention time of 3.13 min. 1H NMR (400 MHz, CD2Cl2) data were as follows: δ 3.84 (s, 3H), 3.90 (s, 3H), 7.12-7.20 (m, 2H), 7.62 (d, 1H).

References

[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 4, p. 734 - 740
[2] Patent: WO2006/44775, 2006, A2. Location in patent: Page/Page column 17
[3] Patent: EP1445249, 2004, A1. Location in patent: Page 138

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