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

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

Downstream Products

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

Relevant articles and documents

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

Decarboxylative Borylation of Stabilized and Activated Carbon Radicals

Redox-active esters (RAEs) as active radical precursors have been extensively studied for C?B bond formations. However, the analogous transformations of stabilized radicals from the corresponding acid precursors remain challenging owing to the strong preference towards single-electron oxidation to the stable carbocations. This work describes a general strategy for rapid access to various aliphatic and aromatic boronic esters by mild photoinduced decarboxylative borylation. Both aryl and alkyl radicals could be generated from the leaving group-assisted N-hydroxybenzimidoyl chloride esters, even α-CF3 substituted substrates could be activated for further elaboration.

Sterically Unprotected Nucleophilic Boron Cluster Reagents

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