5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& Chemical Properties

Melting point:

183-187 °C

Boiling point:

438.5±40.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

-1.09±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36/39

WGK Germany 

3

PackingGroup 

III

5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& Usage And Synthesis

Synthesis

Sodium hydride (60% mineral oil dispersion, 0.48 g, 12 mmol, 1.2 eq.) was slowly added to anhydrous ethanol (20 ml) at 0 °C. To the resulting ethanol solution of sodium ethanol was sequentially added 3-chlorophenylhydrazine hydrochloride (1.79 g, 10 mmol, 1.0 eq.) and ethoxymethylene malononitrile (1.22 g, 10 mmol, 1.0 eq.). The reaction mixture was heated to reflux with continuous stirring for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and precipitation was observed to be generated. Anhydrous ethanol (20 ml) was added to the reaction mixture for dilution, the precipitate was collected by filtration, washed with ether (2 x 100 ml) and dried under vacuum to afford the target compound 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carbonitrile as a yellow solid (1.56 g, 7.13 mmol, 72% yield).LCMS analysis: [M + H]+ = 219, retention time Rt = 1.17min, purity 100%.

References

[1] Patent: EP1746099, 2007, A1. Location in patent: Page/Page column 14
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7451 - 7454
[3] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 6, p. 1425 - 1428

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