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Top 4-Hydroxyphenylboronic acid丨CAS 71597-85-8
4-Hydroxyphenylboronic acid (CAS 71597-85-8), also known as 4-hydroxybenzeneboronic acid or 4-boronophenol, is a multifunctional aromatic organoboron compound containing a boronic acid group and a phenolic hydroxyl group at the para-positions of a benzene ring. Its structure combines the carbon–carbon bond-forming utility of an arylboronic acid with the chemical versatility of a phenolic hydroxyl group. This combination makes it a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, functionalized aromatic compounds, polymer modification, and molecular recognition research.
Chemical Identifiers
| InChI | 1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H |
| InChI Key | COIQUVGFTILYGA-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC(=C1)O)B(O)O |
| EC No. | 615-307-0 |
| MDL No. | MFCD01074628 |
| PubChem CID | 2734360 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-Hydroxyphenylboronic acid is a useful coupling partner in Suzuki–Miyaura reactions for preparing hydroxy-substituted biaryl and aryl–heteroaryl compounds. Under suitable 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 protection may be beneficial in certain synthetic routes. Its para-substitution pattern enables the preparation of aromatic frameworks with a hydroxyl group positioned opposite the newly formed carbon–carbon bond.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-Hydroxyphenylboronic acid serves as a building block for introducing a para-hydroxyphenyl fragment into research molecules. Phenolic hydroxyl groups can participate in hydrogen-bonding interactions and influence molecular polarity, solubility, and interactions with biological targets. Through suitable cross-coupling and functionalization reactions, researchers can prepare structurally diverse aromatic compounds for lead optimization and structure–activity relationship studies. The compound also provides a convenient starting point for investigating the effects of hydroxyl substitution on molecular properties.
Applications in Pharmaceutical Intermediate Synthesis
4-Hydroxyphenylboronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing a phenolic hydroxyl group. The boronic acid functionality enables the construction of biaryl and aryl–heteroaryl frameworks, while the hydroxyl group provides opportunities for further transformations. Under appropriately selected conditions, the phenolic group can undergo etherification, esterification, or other suitable functionalization reactions. These capabilities support multistep synthetic pathways and the preparation of diverse pharmaceutical research intermediates.
Applications in Phenolic Ether and Ester Synthesis
The phenolic hydroxyl group makes this compound useful for preparing oxygen-functionalized aromatic derivatives. Through suitable O-alkylation or O-acylation reactions, the hydroxyl group can be converted into ether or ester functionalities. Depending on the reaction conditions, protection or careful control of the boronic acid group may be necessary. These transformations provide additional flexibility for molecular diversification and the development of functionalized aromatic building blocks.
