321574-04-3

Basic information

• Product Name: 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-BROMO-2-METHYLPHENYLBORONIC ACID PINACOL ESTER
• CAS NO: 321574-04-3
• Molecular Formula: C13H18BBrO2
• Molecular Weight: 296.99582
• Mol File: 321574-04-3.mol

Chemical Properties

• Boiling Point: 343.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(321574-04-3)
• EPA Substance Registry System: 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(321574-04-3)

Safety Data

• Hazardous Substances Data: 321574-04-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a reagent in the Suzuki coupling reaction for forming carbon-carbon bonds. This reaction is a widely used method in organic chemistry, facilitating the creation of new chemical entities.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Production:
2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is also utilized in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that can improve crop yields and protect plants from pests.
Used in Electronic Materials Synthesis:
2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is employed in the production of materials for electronic applications, such as organic semiconductors and other components used in electronic devices. Its role in creating these materials is crucial for advancing technology in various electronic industries.

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 116632-39-4 2-methyl-4-bromoiodobenzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 

Relevant articles and documents

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.

METHODS OF MANUFACTURING OF BORON COMPOUND WITHOUT TRANSITION METALS

The present invention refers to aryl boron compound number bath method relates to search, more particularly transition metal catalyst to a tank without the use of boron compounds number is given to the aryl organic halo [ceyn [ceyn] freight method are disclosed to boron. (by machine translation)

Chemoselective coupling of 1,1-bis[(pinacolato)boryl]alkanes for the transition-metal-frec borylation of aryl and vinyl halides: A combined experimental and theoretical investigation

A new transition-metal-frec borylation of aryl and vinyl halides using l,l-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemo-selectivity and functional group compatibility, thus offering a rare example of a transition-metal-frec borylation protocol. Experimental and theoretical studies have becn performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct betwecn organohalides and α-borylcarbanion, generated in situ from the reaction of l,l-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions.

Palladium-catalyzed borylation of aryldiazonium tetrafluoroborate salts. A new synthesis of arylboronic esters

The first synthesis of arylboronic esters via the coupling of bis(pinacolato)diboron with easily prepared aryldiazonium tetrafluoroborate salts is reported. The palladium-catalyzed borylation reaction proceeds efficiently under mild reaction conditions in the absence of a base to afford various functionalized arylboronic esters in moderate to high yields. (C) 2000 Elsevier Science Ltd.