1256781-59-5

Basic information

• Product Name: 2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1256781-59-5
• Molecular Weight: 297
• Mol File: 1256781-59-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1256781-59-5)
• EPA Substance Registry System: 2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1256781-59-5)

Safety Data

• Hazardous Substances Data: 1256781-59-5(Hazardous Substances Data)

Usage

Class

Boronic ester compound

Usage

Reagent for Suzuki-Miyaura cross-coupling reactions

Purpose

Coupling of aryl halide with organoboron compound to form biaryl compound

Applications

Synthesis of pharmaceuticals, agrochemicals, and materials

Value

Construction of carbon-carbon bonds in complex organic molecules

Structure

2-(2-bromo-5-methylphenyl) group attached to a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane group.

Upstream product

• 106-38-7 para-bromotoluene 
• 73183-34-3 bis(pinacol)diborane 
• 253342-48-2 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane 

Relevant articles and documents

Arene borylation through C–H activation using Cu3(BTC)2 as heterogeneous catalyst

C–H borylation by diborane is an important process to access organoboron compounds. Noble metals, including Ir and Rh-based complexes either in the form of homogeneous or heterogeneous catalysts, have been reported to promote arene C–H borylation. Recently, metal organic frameworks (MOFs) having Ir and Co as active sites have been used as catalysts, but they require co-catalysts. In the present study, commercially available Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) MOF is reported as an effective catalyst to promote borylation of arenes through C–H activation employing bis(pinacolato)diboron (1) as reagent leading to benzylic and aromatic borylation products. Interestingly, other related MOFs like MIL-101(Cr) and Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylate) do not exhibit catalytic activity under identical conditions. Mechanistic studies using in-situ IR spectroscopy reveal that Cu ions play a crucial role in activating the arene and B–B bond in 1.