3-(Hydroxymethyl)phenylboronic Acid | CAS 87199-15-3 | ≥98%

Suzuki–Miyaura cross-coupling reactions: 3-(Hydroxymethyl)phenylboronic acid is a versatile building block in palladium-catalysed Suzuki–Miyaura cross-coupling reactions with aryl halides for the construction of carbon–carbon bonds. The hydroxymethyl group on the arene ring provides a functional handle that can be further derivatised after the coupling step, enabling the introduction of biaryl motifs bearing a primary alcohol into complex molecular frameworks.


Synthesis of biologically active molecules: This compound has been employed as a coupling partner in the synthesis of biologically active scaffolds, including chorismate mutase inhibitors of Mycobacterium tuberculosis H37Rv via Suzuki coupling, pyrrole derivatives, and structurally diverse biaryl intermediates for structure–activity relationship studies in medicinal chemistry programmes.

Copper-mediated and copper-catalysed transformations: 3-(Hydroxymethyl)phenylboronic acid has been used as a reactant in copper-mediated trifluoromethylation reactions and in copper-catalysed transformations of arylboronic acids carried out in aqueous media, broadening its utility beyond traditional palladium catalysis.

Mitsunobu and amidation reactions: The hydroxymethyl substituent allows this boronic acid to participate in Mitsunobu reactions, enabling the conversion of the benzylic alcohol to ethers, esters, or nitrogen-containing functional groups under mild conditions. It has also been used in amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate substrates.

Diol recognition and boronate ester formation: As an arylboronic acid, this compound forms reversible cyclic boronate esters with cis-1,2- and 1,3-diols in aqueous solution. The hydroxymethyl group at the meta position influences the electronic properties and pKa of the boronic acid, which affects the equilibrium and kinetics of boronate ester formation. This property is relevant to the design of boronic acid-based receptors for saccharides and other diol-containing analytes.

Boronic acid-functionalized materials: The bifunctional nature of 3-(hydroxymethyl)phenylboronic acid — combining a boronic acid recognition element with a primary alcohol linker group — makes it a useful monomer or building block for the preparation of boronic acid-functionalized polymers, hydrogels, and surface-modified materials used in affinity chromatography and glycoprotein capture.

Pharmaceutical and agrochemical intermediate: The meta-hydroxymethylphenyl biaryl motif introduced by this boronic acid appears in numerous pharmaceutical and agrochemical intermediates. The compound serves as a convenient, air-stable solid reagent for introducing this structural unit in a single synthetic step.

Note: This product contains varying amounts of the boroxine anhydride, which is the cyclic trimeric anhydride of the boronic acid. This is a common and well-documented property of arylboronic acids and does not affect their reactivity in cross-coupling or esterification reactions.​​​​​​​​​​​​​​​​