5-AMINO-4-CYANO-1-(4-FLUOROPHENYL)PYRAZOLE

5-AMINO-4-CYANO-1-(4-FLUOROPHENYL)PYRAZOLE Property

Melting point:

164-165°C

Boiling point:

394.1±37.0 °C(Predicted)

Density 

1.36±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

-0.92±0.10(Predicted)

form 

solid

Appearance

Yellow to brown Solid

CAS DataBase Reference

51516-70-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

20/21/22-41

Safety Statements 

22-36/37/39-39-26

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933199090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

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

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

5-AMINO-4-CYANO-1-(4-FLUOROPHENYL)PYRAZOLE Chemical Properties,Usage,Production

Uses

5-Amino-1-(4-fluorophenyl)pyrazole-4-carbonitrile was used in the preparation of compounds that were shown to have anti-viral activity against TMV.

Synthesis

GENERAL METHOD: (4-Fluorophenyl)hydrazine (0.001 mol) was mixed with 10 mL of ethanol, stirred and heated to reflux. Subsequently, ethoxymethylene malononitrile (0.001 mol) dissolved in 10 mL of ethanol was added slowly and dropwise. The reaction mixture was kept at reflux for 2 hours. After completion of the reaction, the mixture was poured into 50 mL of ice water. The precipitate was collected by filtration and washed with cold water to afford 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile (10a) in 61% yield. The product characterization data were as follows: melting point: 173-174 °C. IR (cm^-1): 3297-3183 (NH2); 2225 (CN); 1662; 1568. ^1H NMR (400 MHz, DMSO-d6, TMS, δ in ppm): 7.31-7.25 (m, 2H, H3', H5'); 7.54- 7.49 (m, 2H, H2', H6'); 7.67 (s, 1H, H3). ^13C NMR (100 MHz, DMSO-d6, TMS, δ in ppm): 73.2 (C4); 114.8 (CN); 116.3 (d, J = 22.8 Hz, C3', C5'); 126.9 (d, J = 8.9 Hz, C2', C6'); 133.7 (d, J = 2.8 Hz, C1'); 141.7 (C5); 151.4 (C3); 161.2 (d, J = 243.6 Hz, C4'). ^19F NMR (376 MHz, DMSO-d6, TMS, δ in ppm): -114.26. EI-MS [M + 1]^+: 203.07.

References

[1] European Journal of Organic Chemistry, 2018, vol. 2018, # 13, p. 1514 - 1524
[2] Tetrahedron Letters, 2008, vol. 49, # 2, p. 305 - 310
[3] Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1876 - 1884
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2892 - 2898
[5] Organic and Biomolecular Chemistry, 2007, vol. 5, # 17, p. 2758 - 2761