(2-BROMOMETHYLPHENYL)BORONIC ACID, PINACOL ESTER Chemical Properties

Melting point:

78-80°C

Boiling point:

360.6±25.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly)

form 

solid

color 

white to off-white

CAS DataBase Reference

377780-72-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

2

Hazard Note 

Irritant/Keep Cold

TSCA 

No

HS Code 

2931900090

(2-BROMOMETHYLPHENYL)BORONIC ACID, PINACOL ESTER Usage And Synthesis

Uses

2-Bromomethylphenylboronic Acid Pinacol Ester is an intermediate used to prepare [(fluorophenylcarbamoyl)pyridinylsulfanylmethyl]phenylboronic acid and noncompetitive boronic acid antagonist of CXCR1 and CXCR2.

Synthesis

To a three-neck flask equipped with a Dean-Stark splitter was added 30 mL of toluene followed by 2-methylphenylboronic acid (0.21 g, 1.55 mmol) and pinacol (0.22 g, 1.86 mmol). The reaction mixture was heated to reflux for 2 hours. Upon completion of the reaction, the mixture was washed three times with 30 mL of water to remove unreacted pinacol and phenylboronic acid. The organic phase was separated and the toluene solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was dissolved in 50 mL of dichloromethane and washed again with 30 mL of water. Anhydrous sodium sulfate was added to the organic phase to dry, and the dried solution was evaporated under reduced pressure to give 0.32 g of crude product. The resulting crude product (0.32 g, 1.47 mmol), N-bromosuccinimide (NBS, 0.39 g, 2.2 mmol) and azobisisobutyronitrile (AIBN, 0.003 g, 0.018 mmol) were dissolved in 10 mL of acetonitrile. The reaction solution was refluxed at 90 °C for 2 hours. After the reaction was completed, it was cooled to room temperature and the solvent was removed by distillation under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether (60~90 °C)/ethyl acetate (v/v = 1:1) as eluent to obtain the target product 2-bromoethylphenylboronic acid pinacol ester as white solid (0.53 g, 80% yield).

References

[1] Patent: CN107383078, 2017, A. Location in patent: Paragraph 0058; 0063; 0064; 0065; 0066; 0067; 0068

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