4-BROMO-3-PHENYL-1H-PYRAZOLE Chemical Properties

Melting point:

116-117 °C(Solv: ethanol (64-17-5))

Boiling point:

365.8±22.0 °C(Predicted)

Density 

1.565±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

12.23±0.50(Predicted)

color 

White to Light yellow

Safety Information

HS Code 

2933199090

4-BROMO-3-PHENYL-1H-PYRAZOLE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-bromo-3-phenyl-1H-pyrazole from 3-phenyl-1H-pyrazole was as follows: 3-phenyl-1H-pyrazole (4.08 g, 28.3 mmol) and N-bromosuccinimide (NBS, 5.04 g, 28.3 mmol) were dissolved in N,N-dimethylformamide (DMF, 40 mL), and the reaction was stirred for 1 h at room temperature. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate (AcOEt). The organic phases were combined, washed sequentially with water and saturated saline, dried over anhydrous magnesium sulfate (MgSO?) and concentrated under reduced pressure to remove the solvent. The resulting residue was recrystallized by hexane/ethyl acetate mixed solvent to give the title compound 4-bromo-3-phenyl-1H-pyrazole (5.84 g, 93% yield) as a white solid with a melting point of 114-116 °C. The NMR hydrogen spectrum (300 MHz, CDCl?) data were as follows: δ 7.39-7.50 (m, 3H), 7.64 (s, 1H), 7.77 (d, J = 6.8 Hz, 2H), 10.73 (brs, 1H).

References

[1] Patent: US2010/197651, 2010, A1. Location in patent: Page/Page column 68
[2] Patent: WO2008/150827, 2008, A1. Location in patent: Page/Page column 57
[3] Inorganica Chimica Acta, 2010, vol. 363, # 7, p. 1332 - 1342
[4] Tetrahedron Letters, 2017, vol. 58, # 43, p. 4111 - 4114
[5] Chemische Berichte, 1895, vol. 28, p. 688

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