[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid Chemical Properties

Boiling point:

572.6±60.0 °C(Predicted)

Density 

1.21

storage temp. 

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

form 

powder to crystal

pka

8.37±0.16(Predicted)

color 

White to Almost white

Safety Information

HS Code 

2933998090

[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid Usage And Synthesis

Application

[4-(2-phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid is an organic synthesis intermediate and a pharmaceutical intermediate that can be used in laboratory research and development processes and chemical production processes.

Synthesis

Under argon protection, 10 g (29 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole was dissolved in 100 mL of anhydrous tetrahydrofuran and the solution was cooled to -78 °C. Subsequently, 20 mL of n-butyllithium solution (1.6 mol/L, dissolved in hexane) was added slowly and dropwise. The reaction mixture was continuously stirred at -78 °C for 1 h and then warmed up to 0 °C. The mixture was again cooled to -78 °C and 9.7 mL (87 mmol) of trimethoxyborane was added dropwise. The mixture continued to be stirred at -78 °C for 1 hour, followed by 2 hours at room temperature. Upon completion of the reaction, 100 mL of 10% (w/w) hydrochloric acid solution was added and stirred for 1 hr, followed by filtration. The organic layer was separated, washed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography to give 4.2 g of [4-(2-phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid in 46% yield.

References

[1] Patent: EP1734038, 2006, A1. Location in patent: Page/Page column 49

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