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

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 591-19-5 m-Bromoaniline 
• 22092-92-8 diisopropopylaminoborane 
• 108-36-1 1,3-dibromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 585-76-2 m-bromobenzoic acid 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 2905-24-0 3-Bromobenzenesulfonyl chloride 
• 89520-70-7 sodium 3-bromobenzenesulfinate 
• 108-86-1 bromobenzene 
• 591-18-4 1-Bromo-3-iodobenzene 
• 2890-88-2 (C₂H₅)3N*BCl₃ 

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 
• 668438-40-2 4-bromo-(2-(3-bromophenyl))pyridine 
• 4373-60-8 2-(3-bromophenyl)pyridine 
• 1310404-86-4 tert-butyl 4-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl) piperidine-1-carboxylate 
• 885594-74-1 tert-butyl N-[3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propyl]carbamate 

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.

Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps

The saturated trihydride IrH3{κ3-P,O,P-[xant(PiPr2)2]} (1; xant(PiPr2)2=9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates the B?H bond of two molecules of pinacolborane (HBpin) to give H2, the hydride-boryl derivatives IrH2(Bpin){κ3-P,O,P-[xant(PiPr2)2]} (2) and IrH(Bpin)2{κ3-P,O,P-[xant(PiPr2)2]} (3) in a sequential manner. Complex 3 activates a C?H bond of two molecules of benzene to form PhBpin and regenerates 2 and 1, also in a sequential manner. Thus, complexes 1, 2, and 3 define two cycles for the catalytic direct C?H borylation of arenes with HBpin, which have dihydride 2 as a common intermediate. C?H bond activation of the arenes is the rate-determining step of both cycles, as the C?H oxidative addition to 3 is faster than to 2. The results from a kinetic study of the reactions of 1 and 2 with HBpin support a cooperative function of the hydride ligands in the B?H bond activation. The addition of the boron atom of the borane to a hydride facilitates the coordination of the B?H bond through the formation of κ1- and κ2-dihydrideborate intermediates.

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.