1-(ETHOXYCARBONYLMETHYL)-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER Chemical Properties

Boiling point:

390.8±22.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

refractive index 

n20/D 1.4814

Flash point:

110 °C

storage temp. 

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

form 

liquid

pka

1.49±0.10(Predicted)

Appearance

Light yellow to yellow Liquid

InChIKey

YUEZJHOSHBTWPV-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933199090

1-(ETHOXYCARBONYLMETHYL)-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER Usage And Synthesis

Chemical Properties

liquid

Uses

1-(Ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol ester

Synthesis

The general procedure for the synthesis of 1-(ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol ester from ethyl 4-bromo-1H-pyrazole-1-acetate and bis-boronic acid pinacol ester was carried out as follows: firstly, 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaboro Heterocyclopentane (436 mg, 1.72 mmol) was dissolved in DMF (10 mL). Subsequently, KOAc (420 mg, 4.29 mmol) and Pd(dppf)Cl2-CH2Cl2 (35 mg, 0.043 mmol) were added sequentially. The reaction mixture was heated to 80 °C and a solution of ethyl 4-bromo-1H-pyrazole-1-acetate (333 mg, 1.43 mmol) in DMF (10 mL) was added dropwise at this temperature. The reaction mixture was stirred at 80 °C overnight and then evaporated to dryness. Finally, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether = 1:10) to afford the target product 1-(ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol ester (76 mg, 19% yield).

References

[1] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 52
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6804 - 6820

1-(ETHOXYCARBONYLMETHYL)-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER(864754-16-5)Related Product Information

• 1H-PYRAZOLE-4-BORONIC ACID
• 1-Ethyl-1H-pyrazole-4-boronic acid, pinacol ester
• 4-Pyrazoleboronic acid pinacol ester
• 1-Methyl-4-pyrazole boronic acid pinacol ester
• 1-(ETHOXYCARBONYLMETHYL)-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER
• 1-Methyl-1H-pyrazole-4-boronic acid