| Identification | Back Directory | [Name]
5-Bromo-thiophene-2-carboxylic acid methyl ester | [CAS]
62224-19-5 | [Synonyms]
5-broMo-
Methyl 2-broMothiophene-5...
2-Bromo-5-(methoxycarbonyl)thiophene
Methyl 2-broMothiophene-5-carboxylate
Methyl 5-bromo-2-thiophenecarboxylate
methyl 5-bromothiophene-2-carboxylate
5-bromo-2-thiophenecarboxylic acid methyl ester
5-Bromo-thiophene-2-carboxylic acid methyl ester
2-Thiophenecarboxylic acid, 5-bromo-, methyl ester | [Molecular Formula]
C6H5BrO2S | [MDL Number]
MFCD03233845 | [MOL File]
62224-19-5.mol | [Molecular Weight]
221.07 |
| Chemical Properties | Back Directory | [Melting point ]
87-88℃ | [Boiling point ]
251.9±20.0 °C(Predicted) | [density ]
1.662±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [Appearance]
Off-white to light brown Solid | [InChI]
InChI=1S/C6H5BrO2S/c1-9-6(8)4-2-3-5(7)10-4/h2-3H,1H3 | [InChIKey]
QLWUHAQCKDHUNL-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)SC(Br)=CC=1 |
| Hazard Information | Back Directory | [Uses]
Methyl 5-Bromo-2-thiophenecarboxylate is used as a reagent in the synthesis of trisubstituted isoxazole derivatives which are novel nonsteroidal antagonists of Farnesoid X Receptor (FXR). FXR plays an important role in regulation of cholesterol, lipid and glucose metabolism. | [Synthesis Reference(s)]
Journal of Medicinal Chemistry, 35, p. 1109, 1992 DOI: 10.1021/jm00084a016 | [Synthesis]
General procedure for the synthesis of methyl 5-bromothiophene-2-carboxylate from methanol and 5-bromo-2-carboxythiophene: 950 mg (4.62 mmol) of 5-bromo-2-carboxythiophene was accurately weighed and dissolved in 10 mL of methanol. Under stirring conditions, 2 ml of sulfoxide chloride (SOCl2) was slowly added dropwise to the solution. After completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, the solvent was removed by evaporation under reduced pressure. The residue was dissolved in an appropriate amount of toluene and dried by evaporation under reduced pressure, this process was repeated three times to completely remove the residual sulfoxide chloride and methanol. The intermediate 5-bromothiophene-2-carboxylic acid methyl ester was finally obtained as 1.0 g in 100% yield. | [References]
[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1109 - 1116
[2] Patent: CN103992311, 2017, B. Location in patent: Paragraph 0103; 0114; 0115; 0116
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 38, p. 6817 - 6820
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
[5] Journal of Materials Chemistry A, 2013, vol. 1, # 34, p. 10008 - 10015 |
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