3-Bromophenylboronic Acid | CAS 89598-96-9 | ≥97%

Suzuki–Miyaura Cross-Coupling

• Widely applied bifunctional arylboronic acid for the construction of meta-bromophenyl biaryl and heteroaryl frameworks via palladium-catalysed Suzuki–Miyaura cross-coupling — the boronic acid group undergoes transmetalation with palladium, enabling efficient carbon–carbon bond formation with aryl halides, vinyl halides, and triflates under a broad range of reaction conditions
• Compatible with aqueous, microwave-assisted, ligand-free, and base-free Suzuki protocols, and with electrophilic coupling partners including aryl chlorides, bromides, iodides, and triflates
• The retained aryl bromide at the 3-position after Suzuki coupling provides a handle for iterative cross-coupling sequences — enabling sequential introduction of two different aryl or heteroaryl groups from a single building block in one-pot or stepwise multi-component strategies

Bifunctional Iterative Synthesis

• One of the most strategically valuable arylboronic acids for complex molecule assembly — the orthogonal reactivity of the boronic acid and aryl bromide groups allows selective engagement of each functional group under different catalytic conditions, enabling divergent synthesis of structurally diverse biaryl and teriaryl frameworks
• The aryl bromide can be engaged in subsequent palladium-catalysed cross-coupling reactions (Suzuki, Negishi, Kumada, Buchwald–Hartwig), copper-mediated Chan–Lam coupling, directed ortho-metalation, or Grignard exchange — providing exceptional synthetic flexibility from a single commercially available precursor
• Applied in the synthesis of anthranilamide-protected arylboronic acids and other protected boronic acid intermediates used as masked coupling partners in multi-step synthesis workflows

Medicinal Chemistry & Drug Discovery

• Key building block for the introduction of meta-bromophenyl motifs into pharmaceutical lead compounds and drug candidates — the bromine atom at the meta position contributes to lipophilicity, metabolic stability profiling, and serves as a traceable handle for further structural elaboration in structure-activity relationship studies
• Applied in the synthesis of biaryl scaffolds, heterocyclic frameworks, and amino acid analogues used as molecular tools in receptor pharmacology and chemical biology research at the synthetic chemistry level

Additional Synthetic Applications

• Reactant in oxidative cross-coupling reactions for the formation of complex biaryl and heterobiaryl structures under copper or palladium catalysis without requiring pre-functionalised coupling partners
• Applied in gold salt-catalysed homocoupling reactions, 1,4-conjugate addition reactions with α,β-unsaturated carbonyl compounds under rhodium catalysis, and enantioselective addition reactions for the construction of chiral biaryl and diarylmethane frameworks
• Used in C–H functionalisation of quinones and other electron-deficient aromatic systems, enabling direct introduction of the meta-bromophenyl group without prior halogenation of the substrate

Boronate Esters & Further Transformations

• Precursor for meta-bromophenyl boronate esters (pinacol, MIDA, neopentyl glycol esters) applied in iterative cross-coupling and complex molecule assembly workflows where the masked boronic acid is revealed selectively in the presence of the aryl bromide
• The aryl bromide can be converted to aryl lithium or Grignard species for addition reactions, or transformed to phenol, amine, nitrile, or other functional groups via classical or metal-mediated substitution — providing broad structural diversification from a single starting material