477841-90-0

Basic information

• Product Name: 4-Bromobenzylboronic acid pinacol ester
• Synonyms: 4-bromobenzylboronic acid pinacol ester;2-(4-Bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(4-broMophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 477841-90-0
• Molecular Formula: C₁₃H₁₈BBrO₂
• Molecular Weight: 297
• Mol File: 477841-90-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 321 °C
• Flash Point: 148 °C
• Appearance: /
• Density: 1.26
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Bromobenzylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromobenzylboronic acid pinacol ester(477841-90-0)
• EPA Substance Registry System: 4-Bromobenzylboronic acid pinacol ester(477841-90-0)

Safety Data

• Hazardous Substances Data: 477841-90-0(Hazardous Substances Data)

Usage

General Description

4-Bromobenzylboronic acid pinacol ester is a boronic acid derivative used in organic synthesis and medicinal chemistry research. It is a white solid compound that is soluble in organic solvents such as dichloromethane and methanol. 4-Bromobenzylboronic acid pinacol ester has the ability to form stable complexes with diols and is commonly used as a reagent for Suzuki-Miyaura cross-coupling reactions to synthesize various biaryl compounds. It can also be utilized in the synthesis of pharmaceuticals and agrochemicals due to its versatility in forming C-C bonds and its potential as a building block in organic synthesis. Additionally, 4-Bromobenzylboronic acid pinacol ester has been investigated for its potential anticancer properties and shows promise as a lead compound for the development of new anticancer agents.

Upstream product

• 589-15-1 1-bromomethyl-4-bromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 1122-91-4 4-bromo-benzaldehyde 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 5467-74-3 4-Bromophenylboronic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 106-38-7 para-bromotoluene 

Downstream Products

• 873-75-6 4-bromobenzenemethanol 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 

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.

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.

Sterically Unprotected Nucleophilic Boron Cluster Reagents

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