1-Boc-pyrazole-4-boronic acid pinacol ester Chemical Properties

Melting point:

82-86 °C (lit.)

Boiling point:

387.9±34.0 °C(Predicted)

Density 

1.09±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

pka

-1.20±0.12(Predicted)

form 

Crystalline Powder

color 

White to beige

Water Solubility 

insoluble

InChI

InChI=1S/C14H23BN2O4/c1-12(2,3)19-11(18)17-9-10(8-16-17)15-20-13(4,5)14(6,7)21-15/h8-9H,1-7H3

InChIKey

IPISOFJLWYBCAV-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C=C(B2OC(C)(C)C(C)(C)O2)C=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1-Boc-pyrazole-4-boronic acid pinacol ester Usage And Synthesis

Chemical Properties

white to beige crystalline powder

Uses

1-Boc-pyrazole-4-boronic Acid Pinacol Ester is used as a reagent in the synthesis of several inhibitors including thieno[3,2-c]pyridin-4-amines which are a novel series of Bruton’s tyrosine kinase (BTK) inhibitors which can be used in drug design.

Synthesis

4-Pyrazoleboronic acid pinacol ester (1.16 g, 6.0 mmol) and di-tert-butyl dicarbonate (1.58 g, 7.2 mmol) were used as raw materials and dissolved in dichloromethane (40 mL). A catalytic amount of 4-dimethylaminopyridine (102 mg, 0.84 mmol) was added and the reaction was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction system and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride solution and then the solvent was removed by rotary evaporation to give the crude product 1-Boc-pyrazole-4-boronic acid pinacol ester (1.5 g, 85% yield).

References

[1] Patent: CN103936728, 2016, B. Location in patent: Paragraph 0177; 0203; 0204; 0205
[2] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 68
[3] Patent: WO2018/154466, 2018, A1. Location in patent: Paragraph 001162; 001164; 001165
[4] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 58
[5] Patent: WO2004/56727, 2004, A2. Location in patent: Page 97

1-Boc-pyrazole-4-boronic acid pinacol ester(552846-17-0)Related Product Information

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• Methyl acrylate
• 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
• Zolpidem tartrate
• Pyrazole
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• NICKEL CARBONYL
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• 1-Methyl-1H-pyrazole-4-boronic acid
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• 1H-PYRAZOLE-4-BORONIC ACID
• 1-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acid
• 4-Pyrazoleboronic acid pinacol ester