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Purchase Bulk (3-hydroxyphenyl)boronic Acid丨CAS 87199-18-6
(3-Hydroxyphenyl)boronic acid (CAS 87199-18-6), also known as 3-hydroxybenzeneboronic acid or 3-boronophenol, is a multifunctional aromatic organoboron compound containing a boronic acid group and a phenolic hydroxyl group at the meta-positions of a benzene ring. The compound combines the synthetic utility of an arylboronic acid with the chemical reactivity and hydrogen-bonding characteristics of a phenol. Its two functional groups enable different synthetic transformations, making it a useful building block for pharmaceutical intermediate development, medicinal chemistry, functionalized aromatic compounds, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H7BO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8-10H |
| InChI Key | WFWQWTPAPNEOFE-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC(O)=C1)O |
| EC No. | 677-211-5 |
| MDL No. | MFCD01074603 |
| PubChem CID | 2734359 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(3-Hydroxyphenyl)boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing hydroxy-substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. The phenolic hydroxyl group may remain available for subsequent modification, although protecting-group strategies may be beneficial in certain synthetic routes. This approach enables the introduction of a meta-hydroxyphenyl fragment into more complex aromatic structures.
Applications in Medicinal Chemistry
Phenolic hydroxyl groups are frequently investigated in medicinal chemistry because they can participate in hydrogen-bonding interactions and influence molecular polarity. (3-Hydroxyphenyl)boronic acid provides a building block for incorporating a hydroxyl-substituted aromatic fragment into candidate molecules. Researchers can use it to prepare structurally related compounds and evaluate the influence of phenolic substitution on molecular properties and biological interactions. These applications support lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
(3-Hydroxyphenyl)boronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing a phenolic hydroxyl group. Its boronic acid functionality enables carbon–carbon bond construction, while the hydroxyl group provides a site for further transformations. Depending on the synthetic route, the phenolic group may undergo etherification, esterification, or other suitable functionalization reactions. This combination allows chemists to develop multistep synthetic pathways from a common aromatic intermediate.
Applications in Phenolic Ether and Ester Synthesis
The phenolic hydroxyl group makes this compound useful for preparing functionalized aromatic ethers and esters. Through suitable O-alkylation or O-acylation reactions, the hydroxyl group can be converted into different oxygen-containing substituents. These transformations may be performed at an appropriate stage of synthesis, with protection or control of the boronic acid functionality when necessary. The resulting derivatives can serve as intermediates for further coupling reactions or molecular diversification.
