Methyl 3-bromo-4-hydroxybenzoate Chemical Properties

Melting point:

108-110℃

Boiling point:

283.1±20.0 °C(Predicted)

Density 

1.627±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

6.82±0.18(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C8H7BrO3/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4,10H,1H3

InChIKey

RKUNSPWAQIUGEZ-UHFFFAOYSA-N

SMILES

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

Safety Information

RIDADR 

UN2811

HS Code 

2918290090

Methyl 3-bromo-4-hydroxybenzoate Usage And Synthesis

Uses

A reactant used in the preparation of selective inhibitors. In unsymmetrical Ullman reaction between methyl 5bromovanillate (II) and methyl 3-bromo-4-hydroxybenzoate (III) yielded all the three possible dicarbomethoxy-dibenzo-pdioxms which were separated by repeated chromatography over silica gel. A phosphorus- and bromine-containing bifunctional monomer has been prepared from bis(chloromethyl)methylphosphine oxide and the sodium salt of methyl 3-bromo-4-hydroxybenzoate.

Synthesis

The general procedure for the synthesis of methyl 3-bromo-4-hydroxybenzoate from methanol and 3-bromo-4-hydroxybenzoic acid is as follows: 1. Preparation of intermediate T3.1 (methyl 3-bromo-4-hydroxybenzoate): - Under stirring conditions, 3-bromo-4-hydroxybenzoic acid (50.0 g, 231 mmol) was dissolved in methanol (300 mL). - To the above solution was slowly added cold sulfuric acid solution (2.50 mL, 47 mmol). - The reaction mixture was heated to 80 °C and the progress of the reaction was monitored by thin layer chromatography (TLC). - After 16.5 h of reaction, the solvent was removed by distillation under reduced pressure. - The reaction mixture was diluted with ethyl acetate (EtOAc). - The organic phase was sequentially washed twice with saturated aqueous sodium bicarbonate (NaHCO3), once with brine and then dried with anhydrous sodium sulfate. - After filtration, the organic solvent was removed by distillation under reduced pressure to give the intermediate T3.1 as a white solid in 100% yield, which can be used in the next reaction without further purification.

References

[1] Patent: WO2010/45258, 2010, A2. Location in patent: Page/Page column 119
[2] Patent: WO2009/111056, 2009, A1. Location in patent: Page/Page column 103; 141
[3] Patent: WO2017/36404, 2017, A1. Location in patent: Paragraph 57; 58
[4] Patent: EP2380890, 2011, A1. Location in patent: Page/Page column 35
[5] Macromolecules, 2003, vol. 36, # 12, p. 4328 - 4336

Methyl 3-bromo-4-hydroxybenzoate(29415-97-2)Related Product Information

• methyl 3-bromo-1-(difluoromethyl)-1H-pyrazole-5-carboxylate
• Methyl 3-bromo-4-methylbenzoate
• 3-BROMO-4-FLUORO-BENZOIC ACID METHYL ESTER
• 3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER
• methyl 3-bromo-5-chloro-2-methylbenzoate
• Methyl 3-bromo-5-iodobenzoate
• 3-BroMo-5-cyanobenzoic acid Methyl ester
• METHYL 3-BROMO-6-FLUORO-2-METHYLBENZOATE
• METHYL 3-BROMO-5-CHLOROBENZOATE
• Methyl 3-bromo-4-(trifluoromethyl)benzoate
• methyl 3-bromo-5-fluoro-2-methylbenzoate
• Methyl 3-BroMo-5-forMylbenzoate
• 3-Bromo-2-fluorobenzoic acid methyl ester
• 3-Bromo-4-hydroxybenzonitrile