1-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Chemical Properties

Boiling point:

389.8±15.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

-0.58±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C15H19BN2O2/c1-14(2)15(3,4)20-16(19-14)12-10-17-18(11-12)13-8-6-5-7-9-13/h5-11H,1-4H3

InChIKey

XPAJFLOIPDXRRD-UHFFFAOYSA-N

SMILES

N1(C2=CC=CC=C2)C=C(B2OC(C)(C)C(C)(C)O2)C=N1

Safety Information

HS Code 

2933199090

1-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Usage And Synthesis

Synthesis

The general procedure for the synthesis of 1-phenyl-1H-pyrazole-4-boronic acid pinacol ester from 4-bromo-1-phenyl-1H-pyrazole and biboronic acid pinacol ester was as follows: to a solution of 4-bromo-1-phenyl-1H-pyrazole (0.5 g, 2.3 mmol) in DMSO (50 mL) was added sequentially at room temperature KOAc (0.66 g, 6.8 mmol), bis( pinacolato) diboron (0.63 g, 2.5 mmol) and PdCl2(dppf) (0.076 g, 0.11 mmol). The reaction mixture was stirred at 80 °C overnight. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (eluent ratio: ethyl acetate:petroleum ether = 1:12) to afford 1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.3 g, 50% yield) as a light yellow solid.

References

[1] Patent: WO2009/155527, 2009, A2. Location in patent: Page/Page column 134

1-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(1002334-12-4)Related Product Information

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