METHYL 3-METHYLTHIOPHENE-2-CARBOXYLATE Chemical Properties

Boiling point:

216-217°C

Density 

1.173±0.06 g/cm3(Predicted)

refractive index 

1.5168

Flash point:

216-217°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow

BRN 

116836

InChI

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

InChIKey

BRWROFVPMUPMJQ-UHFFFAOYSA-N

SMILES

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

Safety Information

Safety Statements 

23-24/25

HS Code 

29151300

MSDS

• Language:English Provider:ALFA

METHYL 3-METHYLTHIOPHENE-2-CARBOXYLATE Usage And Synthesis

Chemical Properties

Colorless liquid

Synthesis

Step 1: Synthesis of methyl 3-methylthiophene-2-carboxylate: 3-methylthiophene-2-carboxylic acid (15 g, 105 mmol, 1.0 eq.) was dissolved in methanol (150 mL) and concentrated sulfuric acid (7.5 mL) was added slowly and dropwise. The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed sequentially with water (2 x 50 mL), saturated aqueous sodium bicarbonate solution (2 x 50 mL) and brine (50 mL). The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford 20 g (97% yield) of methyl 3-methylthiophene-2-carboxylate as an oil. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.38 (d, J=5.0 Hz, 1H), 6.91 (d, J=5.0 Hz, 1H), 3.85 (s, 3H), 2.55 (s, 3H); ESI-MS m/z 157 ([M+H]+).

References

[1] Patent: WO2012/56478, 2012, A1. Location in patent: Page/Page column 75-76
[2] Patent: WO2007/124546, 2007, A1. Location in patent: Page/Page column 58
[3] Patent: WO2014/64131, 2014, A2. Location in patent: Page/Page column 114; 115
[4] Patent: WO2014/76104, 2014, A1. Location in patent: Page/Page column 79-80
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 24, p. 4806 - 4820

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