ETHYL 2-AMINO-4,5-DIMETHYLTHIOPHENE-3-CARBOXYLATE Chemical Properties

Melting point:

90 °C

Boiling point:

302.9±37.0 °C(Predicted)

Density 

1.185±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

0.56±0.10(Predicted)

color 

White to Light yellow

λmax

310nm(MeOH)(lit.)

InChI

InChI=1S/C9H13NO2S/c1-4-12-9(11)7-5(2)6(3)13-8(7)10/h4,10H2,1-3H3

InChIKey

JYSDXODDWAQWJR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4815-24-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:ALFA

ETHYL 2-AMINO-4,5-DIMETHYLTHIOPHENE-3-CARBOXYLATE Usage And Synthesis

Chemical Properties

Yellow solid

Uses

2-Amino-4,5-dimethyl-3-thiophenecarboxylic Acid Ethyl Ester is used in the preparation triazine and pyrimidine derivatives as anti-inflammatory and analgesic agents. Also used in the synthesis of antioxidants through heteroaryl amines as well as CB2 cannabinoid receptor partial agonists.

Synthesis

To a 100-mL round-bottomed flask were added 2-butanone (20 g, 0.28 mol, 1.0 eq.), ethyl cyanoacetate (31.4 g, 0.28 mol, 1.0 eq.), and sulfur powder (8.9 g, 0.28 mol, 1.0 eq.), followed by ethanol as a solvent. Diethylamine (21 g, 0.28 mol, 1.0 eq.) was added dropwise to the above mixture. The reaction system was stirred continuously for 8 hours at room temperature. After completion of the reaction, the reaction mixture was diluted with water and the resulting precipitate was collected by filtration. Purification by ethanol recrystallization afforded ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate as a yellow solid (41 g, 75% yield).

References

[1] Synthetic Communications, 2012, vol. 42, # 16, p. 2367 - 2374
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2091 - 2092
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 24, p. 4233 - 4242
[4] Journal of Sulfur Chemistry, 2014, vol. 35, # 3, p. 261 - 269
[5] Journal of Heterocyclic Chemistry, 2014, vol. 51, # SUPPL. 1, p. E216-E221

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