3-(Hydroxymethyl)phenylboronic Acid

Technical Specifications

Product Description & Scientific Applications

3-(Hydroxymethyl)phenylboronic Acid is a bifunctional arylboronic acid building block with a meta-substitution pattern placing the boronic-acid and benzylic alcohol handles at a 120° relative disposition.

Applications and Reactions

Suzuki–Miyaura coupling: Couples with aryl, heteroaryl, and alkenyl halides or triflates under standard Pd-catalysed aqueous-basic conditions to give biaryl, heterobiaryl, and styrene-type products; the meta-benzylic alcohol is retained as a post-coupling functional handle.

Hydroxymethyl handle on the free boronic acid: Standard benzylic alcohol chemistry applies — Appel halogenation, mesylation, tosylation, Mitsunobu, etherification, esterification, carbamate formation, controlled oxidation to the aldehyde or acid — within the compatibility limits of any onward steps in the target molecule.

Reversible boronate ester formation with diols: Forms reversible covalent boronate esters with cis-1,2- and 1,3-diols, saccharides, and catechols in aqueous media. The meta-hydroxymethyl group provides an additional alcohol handle for scaffold attachment, surface attachment, or orthogonal modification.

Dynamic-covalent boronate–diol networks: The reversible boronate–diol bond underpins self-healing polymers, pH- and glucose-responsive hydrogels, and crosslinked dynamic networks.

Copper-catalysed transformations of arylboronic acids in water: The Cu2O/ammonia-in-water system converts arylboronic acids to aryl iodides, azides, sulfones, phenols, anilines, and nitroarenes under air, with inorganic salt and ammonia as the functional-group sources.

Copper-mediated trifluoromethylation: Substrate in copper-mediated trifluoromethylation of arylboronic acids, giving the meta-trifluoromethylbenzyl alcohol framework under Cu/CF3-source conditions outside the conventional Pd/aryl-halide manifold.

Chan–Lam-type C–N and C–O coupling: With Cu(OAc)2 or related Cu(II) systems and an amine, amide, sulfonamide, carbamate, phenol, or selected alcohol partner under mild aerobic conditions, gives the corresponding N-aryl or O-aryl product.

Petasis borono-Mannich reaction: The boronic acid acts as the aryl donor in a three-component coupling with an amine and an aldehyde, glyoxylic acid, or α-hydroxy aldehyde partner to give arylated amines, including α-aryl glycine and β-amino alcohol scaffolds.

Protected boronate derivatives: The pinacol ester (Bpin, CAS 443776-76-9) is commercially documented. Other protected forms include the MIDA boronate, neopentyl glycol ester, Bdan, trifluoroborate, and MEA boronate. The MIDA boronate is a chromatographically tractable, air-stable boron surrogate compatible with iterative Suzuki coupling under slow-release conditions; the Bpin ester is a common protected form for handling and cross-coupling.

Non-classical arylation pathways: Arylboronic acids participate in Suzuki–Miyaura-type coupling with arenediazonium salts under Pd catalysis and in base-free Suzuki-type arylation with pentavalent triarylantimony diacetates, giving biaryl products from electrophiles outside the usual aryl halide/triflate set.

Further Reading

Choosing Your Boron Source for Suzuki–Miyaura Coupling.

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