2-Methyl-3-thiophenecarboxylic acid methyl ester Chemical Properties

Boiling point:

90-91 °C(Press: 17 Torr)

Density 

1.173±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C7H8O2S/c1-5-6(3-4-10-5)7(8)9-2/h3-4H,1-2H3

InChIKey

CCNDEWOBDKZGAD-UHFFFAOYSA-N

SMILES

C1(C)SC=CC=1C(OC)=O

Safety Information

RIDADR 

1993

HazardClass 

3

PackingGroup 

Ⅲ

HS Code 

2934999090

2-Methyl-3-thiophenecarboxylic acid methyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 2-methyl-3-thiophenecarboxylate from methanol and 2-methyl-3-thiophenecarboxylic acid: thionyl chloride (200 mL, 2.76 mol) was added slowly and dropwise to a solution of 2-methyl-3-thiophenecarboxylic acid (100 g, 703 mmol) in methanol (500 mL). After stirring the reaction mixture under reflux conditions for 3 h, it was concentrated under reduced pressure. The concentrated residue was diluted with dichloromethane, washed sequentially with water, saturated aqueous sodium bicarbonate solution and brine, and then dried over anhydrous sodium sulfate. After filtration, the solvent was removed by concentration under reduced pressure to give 105 g (96% yield) of methyl 2-methyl-3-thiophenecarboxylate as a brown oil. Its NMR hydrogen spectrum (400 MHz, CDCl3) data were as follows: δ 7.38 (d, J = 5.4 Hz, 1H), 6.98 (d, J = 5.4 Hz, 1H), 3.85 (s, 3H), 2.74 (s, 3H); Mass Spectrometry (ESI) m/z: 157 (M + H)+.

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 269 - 294
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5417 - 5422
[3] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 471 - 476
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 24, p. 4806 - 4820
[5] Patent: US2012/101137, 2012, A1. Location in patent: Page/Page column 14