Ethyl 2-aminothiophene-3-carboxylate

Ethyl 2-aminothiophene-3-carboxylate Property

Melting point:

42 °C

Boiling point:

273.6±20.0 °C(Predicted)

Density 

1.262±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform, Dichloromethane

form 

Solid

pka

0.11±0.10(Predicted)

color 

Brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C7H9NO2S/c1-2-10-7(9)5-3-4-11-6(5)8/h3-4H,2,8H2,1H3

InChIKey

MKJQYFVTEPGXIE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

31891-06-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37-60

HazardClass 

IRRITANT

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Ethyl 2-aminothiophene-3-carboxylate Chemical Properties,Usage,Production

Chemical Properties

Brown Solid

Uses

Ethyl 2-aminothiophene-3-carboxylate is used as an organic chemical synthesis intermediate.

Synthesis

The general procedure for the synthesis of ethyl 2-aminothiophene-3-carboxylate from 1,4-dithio-2,5-diol and ethyl cyanoacetate was as follows: in a 2-5 mL microwave reaction flask, ethyl cyanoacetate (0.22 mmol, 1.0 equiv.) and trifluoroethanol (2 mL) were added, and stirred for 2 min until complete dissolution. Subsequently, 1,4-dithio-2,5-diol (0.11 mmol, 0.5 eq.) was added and stirring was continued for 5 min. Next, triethylamine (0.242 mmol, 1.1 eq.) was added and the reaction mixture was stirred for another 2 minutes. The reaction flask was sealed and placed in a microwave reactor and heated at 60 °C for 390 min. After completion of the reaction, the solvent was removed by vacuum evaporation. The crude product was purified by silica gel fast column chromatography (eluent: ethyl acetate/hexane mixed solvent) to afford the target product ethyl 2-aminothiophene-3-carboxylate.

References

[1] Synthesis (Germany), 2013, vol. 45, # 1, p. 45 - 52
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5437 - 5447
[3] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 875 - 883
[4] Chemical Communications, 2013, vol. 49, # 2, p. 190 - 192
[5] Archiv der Pharmazie, 2011, vol. 344, # 7, p. 459 - 465