Methyl 2-aminothiophene-3-carboxylate Chemical Properties

Melting point:

76-81 °C (lit.)

Boiling point:

259.5±20.0 °C(Predicted)

Density 

1.319±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

0.10±0.10(Predicted)

color 

Beige

InChI

InChI=1S/C6H7NO2S/c1-9-6(8)4-2-3-10-5(4)7/h2-3H,7H2,1H3

InChIKey

DGGJQLCAYQCPDD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4651-81-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

Methyl 2-aminothiophene-3-carboxylate Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Uses

Methyl 2-aminothiophene-3-carboxylate may be used to prepare 3-thiaisatoic anhydride via hydrolysis, followed by the reaction with phosgene.

Definition

ChEBI: Methyl 2-aminothiophene-3-carboxylate is a thiophenecarboxylic acid.

Synthesis

To two 20 mL microwave reaction tubes were added 1,4-dithio-2,5-diol (2.0 g, 13.1 mmol, 1.0 eq.) and methanol (10.5 mL), respectively, and the reaction tubes were sealed. Methyl cyanoacetate (2.32 mL, 26.3 mmol, 2.0 eq.), triethylamine (1.28 mL, 9.20 mmol, 0.7 eq.), and N,N-dimethylformamide (3 drops) were added sequentially through the septum to each reaction tube. The reaction mixture was placed in a microwave reactor and the reaction was heated at 50 °C for 3 min. Upon completion of the reaction, the reaction solutions in the two tubes were combined and left at room temperature to allow the product to precipitate. The precipitate was collected by filtration and washed with cold methanol to afford methyl 2-aminothiophene-3-carboxylate (16as) as a white solid (3.88 g, 24.7 mmol, 94% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1947 - 1953
[2] Patent: WO2015/959, 2015, A1. Location in patent: Page/Page column 47
[3] Tetrahedron Letters, 2007, vol. 48, # 30, p. 5261 - 5264
[4] Tetrahedron, 2012, vol. 68, # 45, p. 9226 - 9233
[5] Patent: WO2005/63734, 2005, A2. Location in patent: Page/Page column 60-61

Methyl 2-aminothiophene-3-carboxylate(4651-81-4)Related Product Information

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