Identification | More | [Name]
Ethyl 2-aminothiophene-3-carboxylate | [CAS]
31891-06-2 | [Synonyms]
2-AMINO-3-ETHOXYCARBONYLTHIOPHENE 2-AMINOTHIOPHENE-3-CARBOXYLATE 2-AMINO-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER AKOS B014694 ART-CHEM-BB B014694 ASINEX-REAG BAS 11719538 BUTTPARK 33\06-04 ETHYL 2-AMINOTHIOPHENE-3-CARBOXYLATE Ethyl 2-amino-3-thiophenecarboxylate Ethy 2-aminothiophene-3-carboxylate | [Molecular Formula]
C7H9NO2S | [MDL Number]
MFCD01566303 | [Molecular Weight]
171.22 | [MOL File]
31891-06-2.mol |
Chemical Properties | Back Directory | [Appearance]
Brown Solid | [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) |
Hazard Information | Back Directory | [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 |
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