1092060-78-0

Basic information

• Product Name: 2-(4-bromophenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• Synonyms: 2-(4-bromophenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• CAS NO: 1092060-78-0
• Molecular Weight: 282.973
• Mol File: 1092060-78-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-bromophenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromophenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane(1092060-78-0)
• EPA Substance Registry System: 2-(4-bromophenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane(1092060-78-0)

Safety Data

• Hazardous Substances Data: 1092060-78-0(Hazardous Substances Data)

Usage

Type of compound

boronic ester

Structure

Contains a boron atom bonded to an oxygen atom and an alkyl or aryl group.

Usage

Organic synthesis as a reagent for Suzuki-Miyaura cross-coupling reactions, important for forming carbon-carbon bonds.

Application

Preparation of pharmaceuticals and agrochemicals.

Importance

Valuable chemical for the production of a wide range of organic compounds and of interest to researchers and chemists in various fields.

Upstream product

• 106-40-1 4-bromo-aniline 
• 230299-21-5 4,4,4',4',6,6'-hexamethyl-2,2'-bi(1,3,2-dioxaborinane)bis(hexyleneglycolato)diboron 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 107-41-5 2-methyl-2,4-pentanediol 
• 5467-74-3 4-Bromophenylboronic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 10199-14-1 4,4,6-trimethyl-1,3,2-dioxaborinane 

Downstream Products

• 2116-36-1 1-benzyl-4-bromo-benzene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 

Relevant articles and documents

Photocatalyzed borylation using water-soluble quantum dots

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Improved preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane and its use in a simple [PdCl2(TPP)2]-catalyzed borylation of aryl bromides and iodides

We describe a convenient preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane (MethylPentaneDiolBorane, MPBH) and demonstrate that it is an excellent reagent for the [PdCl2(PPh3)2]-catalyzed borylation of aryl bromides and iodides. The corresponding boronic esters undergo rapid Suzuki coupling reactions in the presence of cesium fluoride. Thus, MPBH is an excellent alternative to pinacolborane for Pd-catalyzed borylation and cross-coupling reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.