5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE Chemical Properties

Melting point:

132-137 °C (lit.)

Boiling point:

402.0±30.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

-1.12±0.10(Predicted)

form 

Solid

color 

Pale Yellow to Dark Yellow

BRN 

161503

Stability:

Stable

CAS DataBase Reference

5334-43-0(CAS DataBase Reference)

NIST Chemistry Reference

5-Amino-4-cyano-1-phenyl pyrazole(5334-43-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29331990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE Usage And Synthesis

Chemical Properties

Off-White Powder

Uses

Shown to have chemiluminescence activity, antifilarial activity and to possess adenosine receptor affinity.

Definition

ChEBI: 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile is a member of pyrazoles and a ring assembly.

Synthesis

3.2 Synthesis of 5-amino-4-cyano-1-phenyl-1H-pyrazole (3a) Phenylhydrazine (2d) (0.45 mL, 4.2 mmol) was dissolved in ethanol (4 mL) with ethoxymethylene malononitrile (1b) (0.51 g, 4.2 mmol). Microwave irradiation was carried out using a CEM Discover microwave synthesizer at 120 °C for 45 min in a sealed pressure rated Pyrex tube (10 mL) with an initial power setting of 100 W. The reaction was carried out in a compressed air chamber with the microwave irradiated at 120 °C for 1 min. Upon completion of the reaction, the solvent was cooled in a stream of compressed air and subsequently removed by decompression distillation. The product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (5:1 v/v) as eluent to afford 1-phenyl-4-cyano-5-aminopyrazole (0.738 g, 95% yield) as a light brown solid with a melting point of 137-139 °C (literature value: 137 °C). High-resolution mass spectrum (measured value: 185.0827, C10H9N4 [MH]+ calculated value: 185.0822); Fourier transform infrared spectra (KBr, cm?1) νmax: 3302 (NH), 3240 (NH), 2230 (CN), 1577, 1530, 1368; 1H NMR (400 MHz, CDCl3) δ: 7.58 (1H, s, H-3), 7.49-7.37 (5H, m, Ph), 4.52 (2H, br s, disappears after exchange of D2O, NH2); 13C NMR (100 MHz, CDCl3) δ: 141.9 (CH), 135.0 (C), 129.3 (CH), 125.5 (CH), 124.1 ( CH), 121.3 (CH), 115.6 (C), 86.2 (C); low resolution mass spectra (APcI) m/z (relative intensity): 226 ([M + MeCNH]+, 100), 185 ([MH]+, 64).

References

[1] Tetrahedron, 2013, vol. 69, # 39, p. 8429 - 8438
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 3, p. 591 - 599
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 13, p. 1514 - 1524
[4] Synthetic Communications, 2011, vol. 41, # 10, p. 1500 - 1507
[5] Heterocyclic Communications, 2005, vol. 11, # 5, p. 385 - 388

5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE(5334-43-0)Related Product Information

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