594823-67-3

Basic information

• Product Name: 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene
• Synonyms: 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene;3-Bromophenylboronic acid, pinacol ester;2-(3-BroMophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 594823-67-3
• Molecular Formula: C₁₂H₁₆BBrO₂
• Molecular Weight: 282.96924
• Mol File: 594823-67-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 333.2±25.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene(594823-67-3)
• EPA Substance Registry System: 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene(594823-67-3)

Safety Data

• Hazardous Substances Data: 594823-67-3(Hazardous Substances Data)

Usage

General Description

3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene is a chemical compound that is used in the field of organic synthesis. It is a derivative of benzene with a bromo group attached to one of its carbon atoms and a boron-containing group attached to another carbon atom. 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and advanced materials. Its boron-containing group makes it a valuable reagent in Suzuki-Miyaura cross-coupling reactions, which are widely used in the construction of carbon-carbon bonds. Due to its versatility and broad utility, 3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene is an important compound in the field of organic chemistry.

Upstream product

• 591-18-4 1-Bromo-3-iodobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 2905-24-0 3-Bromobenzenesulfonyl chloride 
• 89520-70-7 sodium 3-bromobenzenesulfinate 
• 108-86-1 bromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 585-76-2 m-bromobenzoic acid 
• 108-36-1 1,3-dibromobenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 2890-88-2 (C₂H₅)3N*BCl₃ 
• 1350843-22-9 lutidine 
• 1359224-18-2 Me₂NTol*BCl₃ 
• 22092-92-8 diisopropopylaminoborane 

Downstream Products

• 857934-89-5 phenyl-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol 
• 1256781-64-2 2-(2,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 4373-60-8 2-(3-bromophenyl)pyridine 

Relevant articles and documents

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.

Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions

A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.

Borylation of Diazonium Salts by Highly Emissive and Crystalline Carbon Dots in Water

Efficient borylation reaction of diazonium salts in water is realized for the first time by using easily prepared, highly emissive and crystalline carbon dots. Electron-donating and electron-withdrawing groups on diazonium salts were well tolerated with moderate to good conversion efficiency. Compared with widely used metal complexes, organic dyes and quantum dots, the approach presented herein uses carbon dots, which are nontoxic and possess good biological and medicinal compatibility and high reactivity. Therefore, this approach presents a new prospective use for carbon dots in green chemistry.