BENZYLBORONIC ACID PINACOL ESTER Chemical Properties

Boiling point:

65 °C0.15 mm Hg

Density 

0.980 g/mL at 25 °C

refractive index 

n20/D 1.490

Flash point:

>230 °F

storage temp. 

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

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C13H19BO2/c1-12(2)13(3,4)16-14(15-12)10-11-8-6-5-7-9-11/h5-9H,10H2,1-4H3

InChIKey

YCNQPAVKQPLZRS-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1CC1=CC=CC=C1

CAS DataBase Reference

87100-28-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

23-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2931900090

Storage Class

10 - Combustible liquids

MSDS

• Language:English Provider:SigmaAldrich

BENZYLBORONIC ACID PINACOL ESTER Usage And Synthesis

Uses

Benzylboronic acid pinacol ester finds application in Pd (0)-mediated [11 C] carbonylation reaction.

Synthesis

The compound benzyl bromide (2 g, 11.7 mmol) was dissolved in anhydrous DMF (40 mL), and after the addition of pinacol ester of biboronic acid (4.45 g, 17.5 mmol), cuprous bromide (340 mg, 2.3 mmol), and sodium tert-butoxide (1.69 g, 17.5 mmol), it was protected by exchanging the air in the reaction flask with argon, and the reaction was carried out for 10 hours at 80 ??C. The reaction was carried out at 80??C for 10 hours. The reaction was cooled to room temperature, filtered to remove the insoluble material, the filter cake was washed with a small amount of ethyl acetate, the filtrates were combined and extracted with ethyl acetate by adding an appropriate amount of water. The organic layer was collected and dried with anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (eluent PE/EtOAc = 40:1) to obtain the product colorless oily 1.78 g, yield 70%.

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