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

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[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid Basic information
Application
Product Name:[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid
Synonyms:4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid;[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid;[4-(2-phenyl-1H-1,3-benzodiazol-1-yl)phenyl]boronic acid;(4-(2-Phenyl-1H-benzo[d]iMidazol-1-yl)phenyl)boronic acid;Boronicacid, [4-(2-phenyl-1H-benziMidazol-1-yl)phenyl]- (9CI);[4-(2-Phenyl-1H-benziMidazol-1-yl)phenyl]boronic acid (PBIPBA;Boronic acid,B-[4-(2-phenyl-1H-benziMidazol-1-yl)phenyl]-;4-(2-Phenyl-1H-benzimidazol-1-yl)phenylboronic Acid (contains varying amounts of Anhydride)
CAS:867044-33-5
MF:C19H15BN2O2
MW:314.15
EINECS:
Product Categories:OLED
Mol File:867044-33-5.mol
[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid Structure
[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
pka8.37±0.16(Predicted)
form powder to crystal
color White to Almost white
Safety Information
HS Code 2933998090
MSDS Information
[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
1-(4-Bromophenyl)-2-phenylbenzimidazole

760212-58-6

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

867044-33-5

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
[4-(2-Phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid Preparation Products And Raw materials
Raw materials1-(4-Bromophenyl)-2-phenylbenzimidazole-->Triisopropyl borate-->n-Butyllithium-->Tetrahydrofuran-->Hydrochloric acid-->Hexane-->Trimethyl borate-->Water
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