5-Bromo-thiophene-2-carboxylic acid methyl ester Chemical Properties

Melting point:

87-88℃

Boiling point:

251.9±20.0 °C(Predicted)

Density 

1.662±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

HS Code 

2932990090

5-Bromo-thiophene-2-carboxylic acid methyl ester Usage And Synthesis

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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