2-Amino-5-methyl-3-thiophenecarbonitrile Chemical Properties

Melting point:

101-103°C

Boiling point:

318.5±42.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

0.16±0.10(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C6H6N2S/c1-4-2-5(3-7)6(8)9-4/h2H,8H2,1H3

InChIKey

YGXADLPRHBRTPG-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

138564-58-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-22

Safety Statements 

22-36/37/39

RIDADR 

3276

HazardClass 

IRRITANT

HS Code 

29349990

2-Amino-5-methyl-3-thiophenecarbonitrile Usage And Synthesis

Uses

An Impurity generated in the preparation of Olanzapine (O253750).

Synthesis

General procedure for the synthesis of 2-amino-3-cyano-5-methylthiophene from propionaldehyde and malononitrile: 0.070 g of 4-propylcyclohexanone (0.5 mmol), 0.030 g of malononitrile (0.5 mmol), 0.019 g of powdered sulphur (0.6 mmol), and 0.1 cm3 of NaOH (4 mol/dm3 aqueous solution) in a 1 cm3 choline chloride The mixture/urea was stirred at 60°C for 2-3 hours. The progress of the reaction was monitored by TLC and when the reaction was complete, 5 cm3 of water was added. The solid product was separated by filtration and recrystallized with ethanol if necessary to obtain the pure target compound.

References

[1] Monatshefte fur Chemie, 2017, vol. 148, # 4, p. 711 - 716
[2] Research on Chemical Intermediates, 2018, vol. 44, # 3, p. 2195 - 2213
[3] Patent: WO2008/50341, 2008, A2. Location in patent: Page/Page column 32; 33
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 1953 - 1956
[5] Journal of Pharmaceutical Sciences, 2001, vol. 90, # 3, p. 371 - 388

2-Amino-5-methyl-3-thiophenecarbonitrile(138564-58-6)Related Product Information

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