2-Bromo-3-methoxybenzoic acid

2-Bromo-3-methoxybenzoic acid Property

Melting point:

153-155 °C

Boiling point:

330.7±27.0 °C(Predicted)

Density 

1.625±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

2.73±0.10(Predicted)

color 

Pale Beige

Safety

HS Code 

2916310090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

2-Bromo-3-methoxybenzoic acid Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-bromo-3-methoxybenzoic acid from 2-amino-3-methoxybenzoic acid: 2-amino-3-methoxybenzoic acid (4.00 g, 23.9 mmol) was dissolved in 10% aqueous hydrobromic acid (54 ml) at 0 °C. Subsequently, an aqueous solution of sodium nitrite (1.65 g, 23.9 mmol) (17 ml) was slowly added. A 48% hydrobromic acid solution (22 ml) of copper (I) bromide (3.78 g, 26.3 mmol) was added dropwise to the reaction system under stirring. The reaction mixture was gradually warmed up to 60°C and maintained at this temperature for 2 hours. After completion of the reaction, the mixture was cooled to 0°C and the resulting precipitate was collected by filtration. The precipitate was washed with cold water and purified by recrystallization in water to finally obtain pure 2-bromo-3-methoxybenzoic acid (4.07 g, 74% yield). The product was analyzed by mass spectrometry (EI) and the molecular ion peak (MH+) of C8H7BrO3 was 232.

References

[1] Tetrahedron, 2001, vol. 57, # 23, p. 4967 - 4975
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 40, p. 7257 - 7260
[3] Patent: WO2009/55077, 2009, A1. Location in patent: Page/Page column 388-389
[4] Journal of Medicinal Chemistry, 1984, vol. 27, # 3, p. 363 - 367
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3018 - 3022