3-Cyanophenylboronic Acid | CAS 150255-96-2 | ≥98%

Suzuki–Miyaura Cross-Coupling

• Widely applied electron-poor arylboronic acid for the construction of meta-cyanophenyl biaryl and heteroaryl frameworks via palladium-catalysed Suzuki–Miyaura cross-coupling — the electron-withdrawing cyano group at the 3-position significantly modulates the electronic properties of the aryl ring, influencing transmetalation kinetics and coupling reactivity relative to electron-neutral and electron-rich arylboronic acids
• Compatible with a broad range of Suzuki protocols including aqueous, microwave-assisted, ligand-free, and base-free conditions, and with diverse electrophilic coupling partners including aryl chlorides, bromides, iodides, and triflates
• Applied in the synthesis of meta-cyanophenyl biaryl scaffolds encountered widely in pharmaceutical compound libraries, agrochemical intermediates, and functional organic materials

Medicinal Chemistry & Drug Discovery

• Key building block for the introduction of meta-cyanophenyl motifs into drug candidates and lead compounds — the nitrile group at the meta position contributes to electron-withdrawing character, modulates lipophilicity, and participates in specific binding interactions within protein active sites in structure-activity relationship studies
• Applied in the synthesis of biaryl-based amino acid analogues and heterocyclic scaffolds used as tools in receptor pharmacology and chemical biology research at the molecular level
• The cyano group enables downstream nucleophilic aromatic substitution and directed metalation strategies, providing a versatile handle for further structural elaboration of coupling products

Functional Group Interconversion

• The nitrile group serves as a synthetic precursor to a range of functional groups — hydrolysis affords the corresponding meta-carboxyphenyl boronic acid derivative; catalytic reduction gives the meta-aminophenyl framework; cycloaddition with azides delivers tetrazole-substituted biaryls; condensation with hydroxylamine provides amidoximes and oxadiazole precursors
• This functional versatility makes 3-cyanophenylboronic acid one of the most productive single building blocks for rapid structural diversification in medicinal chemistry and materials chemistry workflows

Materials Science & OLED Applications

• Applied in the synthesis of phenylimidazole-based iridium(III) cyclometallated complexes used as phosphorescent emitters in blue and sky-blue organic light-emitting diode (OLED) devices — the electron-withdrawing cyano substituent tunes the emission wavelength and device efficiency
• Used in the development of conjugated organic materials, functional polymers, and electron-transport layer components where the nitrile group modulates HOMO/LUMO energy levels and solid-state packing behaviour

Boronate Esters & Iterative Synthesis

• Precursor for meta-cyanophenyl boronate esters (pinacol, MIDA, neopentyl glycol esters) applied in iterative cross-coupling strategies and complex molecule assembly workflows
• Applied in diol-sensing and saccharide recognition systems where the boronic acid group forms reversible covalent bonds with 1,2- and 1,3-diols — the electron-withdrawing cyano substituent lowers the pKa of the boronic acid, enhancing binding affinity and selectivity relative to unsubstituted phenylboronic acid