1256781-67-5

Basic information

• Product Name: 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1256781-67-5
• Molecular Weight: 317.418
• Mol File: 1256781-67-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1256781-67-5)
• EPA Substance Registry System: 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1256781-67-5)

Safety Data

• Hazardous Substances Data: 1256781-67-5(Hazardous Substances Data)

Usage

Functional group

Boronic acid derivative.

Usage

Building block for various pharmaceuticals, agrochemicals, and materials.

Reactivity

Potent cross-coupling reagent.

Common reactions

Widely used in Suzuki-Miyaura and other transition metal-catalyzed cross-coupling reactions.

Additional role

Used as a ligand in transition metal-catalyzed coupling reactions.

Unique properties

Valuable tool in the field of organic chemistry.

Primary applications

Formation of carbon-carbon bonds and production of complex organic molecules.

Upstream product

• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 73183-34-3 bis(pinacol)diborane 
• 873-38-1 4-chloro-2-bromoaniline 
• 31928-44-6 2-bromo-4-chloroiodobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1451393-45-5 (2-bromo-4-chlorophenyl)boronic acid 

Relevant articles and documents

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

Use of 2-bromophenylboronic esters as benzyne precursors in the Pd-catalyzed synthesis of triphenylenes

ortho-Substituted aryl boronates are introduced as aryne precursors for transition-metal-catalyzed transformations. On treatment with tBuOK and Pd(0), metal-bound aryne intermediates are formed that undergo effective trimerization to form useful triphenylene compounds. For meta-substituted arynes, the 3:1 product ratio in favor of non-C3 symmetric material is indicative of a benzyne mechanism.