2-Benzyloxyphenylboronic acid Chemical Properties

Melting point:

105-110 °C(lit.)

Boiling point:

428.7±47.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

pka

8.57±0.53(Predicted)

color 

White

BRN 

7813704

CAS DataBase Reference

190661-29-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

IRRITANT, CORROSIVE

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Benzyloxyphenylboronic acid Usage And Synthesis

Chemical Properties

White Solid

Uses

Palladium complex-catalyzed selective hydroxylation ? Palladium(II)-catalyzed oxidative Heck reactions ? Metal-free electrophilic fluorination ? Suzuki-Miyaura cross-coupling reactions

Uses

2-Benzyloxyphenylboronic acid is a reagent used in the preparation of different kinase inhibitors.

Uses

Reactant for:• ;Palladium complex-catalyzed selective hydroxylation1• ;Palladium(II)-catalyzed oxidative Heck reactions2• ;Metal-free electrophilic fluorination3• ;Suzuki-Miyaura cross-coupling reactions4

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 2-benzyloxyphenylboronic acid from 2-benzyloxybromobenzene: 1) 19.93 mL of BuLi (1.6 M hexane solution, 31.9 mM, 1 eq.) was slowly added to a 50 mL THF solution containing 8.4 g of 2-benzyloxybenzene bromide (31.9 mM, 1 eq.) via syringe at -78 °C. Stirring was continued at -78 °C for 30 min to obtain a THF solution of the lithiated derivative. 2) Through a dropping funnel, the above lithiated derivative solution was slowly added dropwise at -78°C to a 50 mL THF solution containing 30 g of B(OiPr)3 (159.5 mM, 5 eq.). 3) After the dropwise addition was completed, the reaction mixture was allowed to gradually warm up to room temperature and stirring was continued for 4 hours. 4) The reaction mixture was poured into 20 mL of 3N HCl to quench the reaction, extracted twice with 50 mL of EtOAc, the organic phases were combined, washed with water, dried over anhydrous MgSO4, and concentrated to dryness under reduced pressure to give 8.53 g of crude product. (5) The crude product was purified by silica gel column chromatography with 9:1 cyclohexane/EtOAc as eluent, and finally 3.6 g of pure product was obtained in 47% yield.

References

[1] Organic Letters, 2004, vol. 6, # 24, p. 4595 - 4597
[2] Patent: US2005/154048, 2005, A1. Location in patent: Page/Page column 17

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