Ethyl 2-aminothiophene-3-carboxylate Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37-60

HazardClass 

IRRITANT

HS Code 

29349990

Ethyl 2-aminothiophene-3-carboxylate Usage And Synthesis

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

Ethyl 2-aminothiophene-3-carboxylate(31891-06-2)Related Product Information

• Methyl 2-aminothiophene-3-carboxylate
• DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE
• ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE
• 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER
• 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
• 2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
• ETHYL 2-AMINO-4,5-DIMETHYLTHIOPHENE-3-CARBOXYLATE
• ETHYL 2-AMINO-5-ETHYLTHIOPHENE-3-CARBOXYLATE
• Ethyl thiophene-3-carboxylate
• ETHYL 2-ACETAMIDO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE
• ETHYL 2-AMINO-4-(2-FURYL)THIOPHENE-3-CARBOXYLATE
• ETHYL 2-AMINO-4-(2-THIENYL)THIOPHENE-3-CARBOXYLATE
• ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate
• ETHYL 2-[(2-CHLOROACETYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE
• ETHYL-2-AMINO-BENZO(B)THIOPHENE-3-CARBOXYLATE
• ETHYL 3-AMINOTHIOPHENE-2-CARBOXYLATE
• Ethyl 3-aminothiophene-2-carboxylate ,97%
• AURORA 3766