4-(Hydroxymethyl)phenylboronic Acid | CAS 59016-93-2 | ≥96%

Suzuki–Miyaura Cross-Coupling

• Widely used arylboronic acid for the palladium-catalysed Suzuki–Miyaura cross-coupling, enabling efficient carbon–carbon bond formation with aryl halides, vinyl halides, and triflates — the para-substituted hydroxymethyl group is fully compatible with standard Suzuki conditions and is orthogonally preserved throughout the coupling event.
• Compatible with aqueous, microwave-assisted, ligand-free, and base-free Suzuki protocols across a broad range of aryl chloride, bromide, iodide, and triflate coupling partners — the para-substitution pattern imposes no steric constraints on the transmetalation step.
• The free –CH₂OH group is retained intact after Suzuki coupling, providing a ready handle for post-coupling elaboration of the assembled biaryl product into aldehydes, carboxylic acids, halides, mesylates, or esters.

Bifunctional Building Block & Hydroxymethyl Group Elaboration

• One of the most synthetically versatile arylboronic acids available — the boronic acid and the benzylic hydroxymethyl group are orthogonally reactive, allowing selective engagement of each functional group independently under complementary reaction conditions.
• The –CH₂OH group serves as a masked aldehyde (via Swern, Dess–Martin, or TEMPO oxidation), a masked carboxylic acid (via two-step oxidation), or a leaving-group precursor (via mesylation, tosylation, or halogenation) — enabling direct structural diversification of the assembled biaryl scaffold.
• Applied in the synthesis of bifunctional linkers, tethered building blocks, and dual-handle intermediates where the boronic acid directs cross-coupling and the hydroxymethyl group anchors the molecule to solid supports, polymers, surfaces, or biomolecules.

Medicinal Chemistry & Drug Discovery

• Established reactant in the synthesis of biologically active compounds — documented applications include the preparation of imidazo[4,5-b]pyrazin-2-ones evaluated as mTOR kinase inhibitors and biaryl scaffolds applied in HIV protease inhibitor programmes targeting drug-resistant viral strains.
• The hydroxymethyl group introduces a primary alcohol pharmacophore directly into the biaryl framework — a motif frequently used in drug candidates as a site for glucuronidation profiling, prodrug esterification, or further elaboration into amides and carbamates during lead optimisation.
• Applied in the assembly of heterocyclic frameworks, peptidomimetics, and amino acid analogues used in receptor pharmacology, target engagement studies, and structure-activity relationship campaigns.

Diol Recognition, Boronate Ester Formation & Sensing

• The boronic acid moiety forms reversible covalent boronate esters with 1,2- and 1,3-diols under mild conditions — exploited in saccharide sensors, glucose-responsive materials, and signal-transduction platforms where diol binding triggers a measurable optical or electrochemical response.
• Used as a key component in biosensor architectures for the selective detection of glucose, dopamine, and other diol-containing biomolecules — the hydroxymethyl group provides an additional attachment point for surface immobilisation without disrupting the boronic acid binding site.
• Applied in the preparation of pinacol, MIDA, and neopentyl glycol boronate esters used as bench-stable masked boronic acid equivalents in iterative cross-coupling and complex molecule assembly workflows.

Bioconjugation, Hydrogels & Materials Science

• Applied as a crosslinking agent in boronic acid-functionalised hydrogels for tissue engineering and controlled drug release — forms dynamic covalent networks with diol-containing polymers (e.g. polyvinyl alcohol) whose crosslink density is responsive to pH and sugar concentration.
• Used in bioconjugation strategies to attach proteins, antibodies, and oligonucleotides to surfaces or nanoparticles via boronate ester linkages — the hydroxymethyl group enables additional covalent attachment chemistry orthogonal to the boronate conjugation site.
• Documented reactant in the synthesis of polyurethanes incorporating spindle-type chromophores, and investigated for antibacterial activity in nanogel-mediated delivery platforms against both Gram-positive and Gram-negative bacterial strains.