4-Bromo-3-methoxybenzoic acid Chemical Properties

Melting point:

221-224

Boiling point:

333.7±27.0 °C(Predicted)

Density 

1.625±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

crystalline solid

pka

3.85±0.10(Predicted)

color 

Off-white

Safety Information

Hazard Codes 

Xi

RIDADR 

UN2811

Hazard Note 

Irritant/Keep Cold

HS Code 

2918999090

4-Bromo-3-methoxybenzoic acid Usage And Synthesis

Uses

4-Bromo-3-methoxybenzoic acid is an important fine organic chemical product, widely used in pharmaceuticals, pesticides, fragrances, petrochemicals and other fields. With the development of science and technology, it is playing an increasingly important role in the synthesis of drugs, liquid crystals and other fields.

Chemical Properties

off-white powder

Synthesis

General procedure for the synthesis of 4-bromo-3-methoxybenzoic acid from methyl 4-bromo-3-methoxybenzoate: To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL) was added methanol (45 mL), water (45 mL), and a 1 M aqueous lithium hydroxide (140 mL) in sequence. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. Water was added to the residue, followed by the dropwise addition of 1 N hydrochloric acid while cooling in an ice bath until the pH of the mixture reached 4. The precipitated solid product was collected by diafiltration, washed with water and dried under reduced pressure to give 10.1 g of the title compound 4-bromo-3-methoxybenzoic acid, which was used in the subsequent reaction without further purification.1H-NMR (300 MHz. DMSO-d6): δ[ppm] = 3.87 (s, 3H), 7.42 (dd, 1H), 7.50 (d, 1H), 7.68 (d, 1H), 13.21 (br s, 1H).

References

[1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[2] Patent: US2003/45557, 2003, A1
[3] Patent: WO2011/64328, 2011, A1. Location in patent: Page/Page column 79-80
[4] Patent: WO2012/143329, 2012, A1. Location in patent: Page/Page column 89
[5] Patent: WO2013/87579, 2013, A1. Location in patent: Page/Page column 96; 97

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