METHYL 5-FORMYL-2-THIOPHENECARBOXYLATE Chemical Properties

Melting point:

102℃

Boiling point:

304.3±27.0 °C(Predicted)

Density 

1.324±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Light brown to off-white Solid

Safety Information

HS Code 

2934999090

METHYL 5-FORMYL-2-THIOPHENECARBOXYLATE Usage And Synthesis

Synthesis Reference(s)

Tetrahedron, 64, p. 688, 2008 DOI: 10.1016/j.tet.2007.11.030

Synthesis

Step 1. 5-formyl-2-thiophenecarboxylic acid (2.34 g, 15 mmol) was dissolved in DMF (25 ml) with sodium carbonate (5.57 g, 52.5 mmol) at 25 °C and iodomethane (1.15 ml, 18 mmol) was added slowly. The reaction mixture was stirred at room temperature for 20 h before the reaction was terminated by addition of water and saturated aqueous NH4Cl solution. The reaction mixture was filtered to collect the solid precipitate to give the crude methyl 5-formylthiophene-2-carboxylate. The filtrate was extracted with EtOAc (3 x 30 ml), the organic phases were combined and washed sequentially with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by fast column chromatography and combined with the previously collected solids to give the final methyl 5-formylthiophene-2-carboxylate as a white solid (1.60 g, 62% yield).ESI-MS (m/z): 171.2 (M+H+).

References

[1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 1, p. 17 - 28
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5982 - 5986
[3] Patent: WO2008/124582, 2008, A1. Location in patent: Page/Page column 130
[4] Patent: US5047554, 1991, A
[5] Patent: US2006/293343, 2006, A1. Location in patent: Page/Page column 89

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