| Identification | Back Directory | [Name]
Methyl 3-bromo-4-hydroxybenzoate | [CAS]
29415-97-2 | [Synonyms]
EOS-61539
Methyl 3-bromo-4-hydroxybenzoa
Methyl3-bromo-4-hydroxybenzoate,98%
Benzoic acid, 3-bromo-4-hydroxy-, methyl ester | [EINECS(EC#)]
220-295-1 | [Molecular Formula]
C8H7BrO3 | [MDL Number]
MFCD06203850 | [MOL File]
29415-97-2.mol | [Molecular Weight]
231.044 |
| Chemical Properties | Back Directory | [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) | [form ]
solid | [pka]
6.82±0.18(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
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