ChemicalBook--->CAS DataBase List--->31891-06-2

31891-06-2

31891-06-2 Structure

31891-06-2 Structure
IdentificationMore
[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 PropertiesBack 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)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-37-60
[WGK Germany ]

WGK 3
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

29349990
[Storage Class]

11 - Combustible Solids
Raw materials And Preparation ProductsBack Directory
[Raw materials]

2,5-Dihydroxy-1,4-dithiane-->Ethyl cyanoacetate-->2,2,2-Trifluoroethanol-->Triethylamine
[Preparation Products]

3-(2-FLUOROBENZYL)THIENO[2,3-D]PYRIMIDIN-4(3H)-ONE-->2-aMinothieno[2,3-d]pyriMidin-4(3H)-one-->3-AMINO-2-METHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE
Hazard InformationBack Directory
[Chemical Properties]

Brown Solid
[Uses]

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

2,5-Dihydroxy-1,4-dithiane

40018-26-6

Ethyl cyanoacetate

105-56-6

Ethyl 2-aminothiophene-3-carboxylate

31891-06-2

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
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl 2-aminothiophene-3-carboxylate(31891-06-2)1HNMR
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