2-AMINO-THIOPHENE-3-CARBOXYLIC ACID AMIDE Chemical Properties

Melting point:

153-155°C

Boiling point:

321.8±22.0 °C(Predicted)

Density 

1.423±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

15.58±0.50(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C5H6N2OS/c6-4(8)3-1-2-9-5(3)7/h1-2H,7H2,(H2,6,8)

InChIKey

WHZIZZOTISTHCT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

14080-51-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37

HazardClass 

IRRITANT

HS Code 

2934999090

2-AMINO-THIOPHENE-3-CARBOXYLIC ACID AMIDE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-aminothiophene-3-amides from 1,4-dithio-2,5-diol and cyanoacetamide: Triethylamine (36 mL, 256 mmol) was added to a solution of ethanol (400 mL) containing 2-cyanoacetamide (10.8 g, 128 mmol) and 1,4-dithiazan-2,5-diol (19.5 g, 128 mmol). The reaction mixture was stirred at room temperature for 5 minutes and then heated to reflux for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered and concentrated in vacuum. The residue was dissolved in ethyl acetate (400 mL) and washed sequentially with 1 M aqueous sodium hydroxide (200 mL), water (2 x 200 mL) and brine (200 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give 2-aminothiophene-3-amide (16 g, 113 mmol, 88% yield) as a light yellow solid.LC-MS [M+H]+ m/z 143.

References

[1] Patent: WO2003/104218, 2003, A1. Location in patent: Page 13
[2] Synthesis (Germany), 2013, vol. 45, # 1, p. 45 - 52
[3] Patent: WO2012/30894, 2012, A1. Location in patent: Page/Page column 87
[4] Tetrahedron Letters, 2007, vol. 48, # 30, p. 5261 - 5264
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6734 - 6750

2-AMINO-THIOPHENE-3-CARBOXYLIC ACID AMIDE(14080-51-4)Related Product Information

• 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXAMIDE
• 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE
• ETHYL 5-METHYL-4-OXO-3,4-DIHYDROTHIENO[2,3-D]-PYRIMIDINE-6-CARBOXYLATE
• 2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXAMIDE
• 5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE
• (1)benzothieno(2,3-d)pyrimidin-4(1h)-one,2,3,5,6,7,8-hexahydro-3-methyl-2-thio
• AKOS 94123
• 2-AMINO-5-METHYL-3-THIOPHENECARBOXAMIDE
• 5-thien-2-ylthieno[2,3-d]pyrimidin-4(3H)-one
• 2-[(CHLOROACETYL)AMINO]THIOPHENE-3-CARBOXAMIDE
• 3-ETHYL-2-MERCAPTO-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE
• AKOS BBS-00007188
• 3-CYCLOHEXYL-2-MERCAPTO-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE
• 7-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-2-[(2,4-DICHLOROBENZYL)SULFANYL]-3-METHYL-5,6,7,8-TETRAHYDROPYRIDO[4',3':4,5]THIENO[2,3-D]PYRIMIDIN-4(3H)-ONE
• AKOS 90535
• 7-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-3-METHYL-2-SULFANYL-5,6,7,8-TETRAHYDROPYRIDO[4',3':4,5]THIENO[2,3-D]PYRIMIDIN-4(3H)-ONE
• AKOS BBS-00007201
• AKOS BBS-00007193