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Purchase Bulk (3-(Hydroxymethyl)phenyl)boronic acid丨CAS 87199-15-3
(3-(Hydroxymethyl)phenyl)boronic acid (CAS 87199-15-3), also known as 3-(hydroxymethyl)benzeneboronic acid or 3-boronobenzyl alcohol, is a multifunctional aromatic organoboron compound containing a boronic acid group and a hydroxymethyl group at the meta-positions of a benzene ring. Its structure combines the carbon–carbon bond-forming utility of an arylboronic acid with the chemical versatility of a primary benzyl alcohol. The boronic acid group enables suitable cross-coupling reactions, while the hydroxymethyl functionality provides opportunities for oxidation, esterification, and other chemical transformations. These characteristics make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, functionalized aromatic compounds, and specialty organic research.
Chemical Identifiers
| InChI | 1S/C7H9BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,9-11H,5H2 |
| InChI Key | HGTDLKXUWVKLQX-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC=C1CO)B(O)O |
| EC No. | 672-931-6 |
| MDL No. | MFCD01317846 |
| PubChem CID | 2734662 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(3-(Hydroxymethyl)phenyl)boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing hydroxymethyl-substituted biaryl and aryl–heteroaryl compounds. Under optimized palladium-catalyzed conditions, the boronic acid group can react with suitable aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation introduces a meta-hydroxymethylphenyl fragment into more complex molecular structures. The benzyl alcohol functionality may remain intact under compatible reaction conditions, allowing subsequent chemical modification.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing aromatic research molecules containing a hydroxymethyl group. Primary alcohol groups can influence molecular polarity, hydrogen-bonding interactions, and physicochemical properties. Through suitable cross-coupling reactions, researchers can incorporate the hydroxymethyl-substituted phenyl fragment into candidate compounds and evaluate its contribution to molecular behavior. These applications support lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
(3-(Hydroxymethyl)phenyl)boronic acid may support pharmaceutical intermediate synthesis requiring aromatic compounds with a reactive primary alcohol group. The boronic acid functionality enables carbon–carbon bond construction, while the hydroxymethyl group provides a site for additional transformations. Under appropriately selected conditions, the alcohol may be oxidized to an aldehyde or carboxylic acid, converted into an ether or ester, or transformed into a suitable leaving-group derivative for further substitution reactions. This flexibility supports multistep synthesis and the preparation of diverse pharmaceutical research intermediates.
Applications in Benzyl Alcohol Derivative Synthesis
The hydroxymethyl functionality makes this compound particularly useful for preparing substituted benzyl alcohol derivatives. Through suitable functionalization reactions, the alcohol group can be converted into oxygen-containing intermediates or used as a starting point for introducing other functional groups. The boronic acid group provides an additional route for modifying the aromatic framework. Depending on reaction compatibility, these transformations may be performed sequentially to construct complex molecules with controlled substitution patterns.
