854636-01-4

Basic information

• Product Name: 2-Bromo-4-methylphenylboronic acid
• Synonyms: 2-Bromo-4-methylphenylboronic acid
• CAS NO: 854636-01-4
• Molecular Formula: C₇H₈BBrO₂
• Molecular Weight: 214.85222
• Mol File: 854636-01-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Bromo-4-methylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-methylphenylboronic acid(854636-01-4)
• EPA Substance Registry System: 2-Bromo-4-methylphenylboronic acid(854636-01-4)

Safety Data

• Hazardous Substances Data: 854636-01-4(Hazardous Substances Data)

Upstream product

• 150-46-9 triethyl borate 
• 71838-16-9 3-bromo-4-iodotoluene 
• 121-43-7 Trimethyl borate 

Downstream Products

• 1595077-97-6 2-(2-bromo-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 89981-02-2 methyl (2-bromo-4-methylphenyl) sulfide 
• 1430-97-3 2-methyl-9H-fluorene 
• 583-68-6 2-bromo-p-toluidine 

Relevant articles and documents

Cyclic Diaryl λ3-Bromanes as Original Aryne Precursors

Despite the widespread application of hypervalent iodines, the corresponding λ3-bromanes are less explored. Herein we report a general, safe, and high-yielding strategy to access cyclic diaryl λ3-bromanes. These unique compounds feature reactivity that is appealing and complementary to that of λ3-iodanes, generating arynes under mild reaction conditions and in the presence of a weak base. Accordingly, formal meta-selective transition-metal-free C–O and C–N couplings may be achieved. Mechanistic studies unambiguously support the aryne generation mechanism.

Use of 2-bromophenylboronic esters as benzyne precursors in the Pd-catalyzed synthesis of triphenylenes

ortho-Substituted aryl boronates are introduced as aryne precursors for transition-metal-catalyzed transformations. On treatment with tBuOK and Pd(0), metal-bound aryne intermediates are formed that undergo effective trimerization to form useful triphenylene compounds. For meta-substituted arynes, the 3:1 product ratio in favor of non-C3 symmetric material is indicative of a benzyne mechanism.