5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE

5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE Chemical Properties,Usage,Production

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