1192051-39-0

Basic information

• Product Name: 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;5-Bromo-2-methylphenylboronic acid pinacol ester
• CAS NO: 1192051-39-0
• Molecular Formula: C₁₃H₁₈BBrO₂
• Molecular Weight: 297
• Mol File: 1192051-39-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 69-70℃
• Boiling Point: 364℃
• Flash Point: 168℃
• Appearance: /
• Density: 1.26
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1192051-39-0)
• EPA Substance Registry System: 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1192051-39-0)

Safety Data

• Hazardous Substances Data: 1192051-39-0(Hazardous Substances Data)

Usage

General Description

2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a boron-containing compound with the chemical formula C14H21BBrO2. It is commonly used as a reagent in organic synthesis, particularly in the field of cross-coupling reactions. 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a boronic ester, which makes it useful in the formation of carbon-carbon bonds. It is a colorless liquid with a molecular weight of 284.14 g/mol and a boiling point of 230-232°C. Due to its unique structure and reactivity, 2-(5-Bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane finds practical applications in pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 106-38-7 para-bromotoluene 
• 73183-34-3 bis(pinacol)diborane 

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.