4-(1H-Pyrazol-1-yl)aniline Chemical Properties

Melting point:

54 °C

Boiling point:

312.0±25.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

4.03±0.10(Predicted)

Appearance

Gray to brown Solid

InChI

InChI=1S/C9H9N3/c10-8-2-4-9(5-3-8)12-7-1-6-11-12/h1-7H,10H2

InChIKey

CSFIQHZIFKIQNO-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(N2C=CC=N2)C=C1

CAS DataBase Reference

17635-45-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

HazardClass 

IRRITANT

HS Code 

2921420090

4-(1H-Pyrazol-1-yl)aniline Usage And Synthesis

Synthesis

GENERAL STEPS: In a typical reaction, 5.0 mg of Pd-gCN catalyst (containing 5.0 wt% Pd) was mixed with 1.0 mM 1-(4-nitrophenyl)-1H-pyrazole in ethanol (2 mL) and 60% hydrazine hydrate solution (2 mM, 1.2 equiv, 0.07 mL). The mixture was placed in a 10 mL round-bottomed flask and reacted at reflux temperature (70°C) for 4 hours, followed by cooling to room temperature. After completion of the reaction, the reaction mixture was filtered and the filtrate was purified by silica gel column chromatography to afford 4-(1H-pyrazol-1-yl)aniline (1-(4-aminophenyl)pyrazole). For dinitroaromatic substrates, 4.0 mM (2.4 eq., 0.14 mL) of 60% hydrazine hydrate solution is required.

References

[1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1935 - 1946
[2] Applied Catalysis A: General, 2016, vol. 523, p. 31 - 38
[3] Patent: EP3159340, 2017, A1. Location in patent: Paragraph 0086; 0091
[4] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0165; 0167
[5] Patent: CN105418590, 2016, A. Location in patent: Paragraph 0152; 0153; 0154

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