1,3-Dimethyl-1H-pyrazole-4-boronic acid,pinacol ester Chemical Properties

Melting point:

73.0 to 77.0 °C

Boiling point:

322.3±30.0 °C(Predicted)

Density 

1.04±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

2.56±0.10(Predicted)

color 

White to Orange to Green

InChIKey

FBNAMBTYMSWTIB-UHFFFAOYSA-N

CAS DataBase Reference

1046832-21-6

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933199090

1,3-Dimethyl-1H-pyrazole-4-boronic acid,pinacol ester Usage And Synthesis

Uses

1,3-Dimethyl-1H-pyrazole-4-boronic acid,pinacol ester

Synthesis

4-Bromo-1,3-dimethyl-1H-pyrazole (5.00 g, 28.60 mmol) and pinacol ester of bisboronic acid (8.71 g, 34.32 mmol) were reacted in anhydrous 1,4-dioxane (100.0 mL). Potassium acetate (5.63 g, 57.41 mmol) and Pd(dppf)Cl2-CH2Cl2 (2.38 g, 2.86 mmol) were added to the reaction system. The reaction mixture was displaced three times with nitrogen to remove air, followed by warming to 100 °C and stirring the reaction overnight. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The concentrated residue was diluted with water (30 mL) and extracted with ethyl acetate (50 mL x 3). The organic layers were combined and dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether) to afford the target product 1,3-dimethylpyrazole-4-boronic acid pinacol ester as a brown viscous liquid (3.80 g, 60% yield).

References

[1] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0297
[2] Patent: CN108570048, 2018, A. Location in patent: Paragraph 0590; 0592-0593
[3] Patent: WO2018/169700, 2018, A1. Location in patent: Page/Page column 00343
[4] Patent: US2013/123281, 2013, A1. Location in patent: Paragraph 0127; 0128

1,3-Dimethyl-1H-pyrazole-4-boronic acid,pinacol ester(1046832-21-6)Related Product Information

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