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Purchase Online (5-Chloro-2-hydroxyphenyl)boronic Acid丨CAS 89488-25-5
(5-Chloro-2-hydroxyphenyl)boronic acid (CAS 89488-25-5) is a functionalized aromatic boronic acid containing a chlorine atom at the 5-position, a hydroxyl group at the 2-position, and a boronic acid functionality attached to the benzene ring. The combination of organoboron, phenolic, and halogen functionalities makes this compound a useful building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty chemical research. Its boronic acid group can participate in carbon–carbon bond-forming reactions, while the hydroxyl and chlorine substituents provide additional structural features for molecular modification and synthetic diversification.
Chemical Identifiers
| InChI | InChI=1S/C6H6BClO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9-11H |
| InChI Key | GGZASRFCRAZNPO-UHFFFAOYSA-N |
| Smiles | OB(C1=CC(Cl)=CC=C1O)O |
| EC No. | 639-351-5 |
| MDL No. | MFCD06659863 |
| PubChem CID | 23005362 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(5-Chloro-2-hydroxyphenyl)boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare substituted biaryl compounds and other aromatic structures. Under appropriately selected catalytic conditions, the boronic acid functionality can react with compatible organic halides or pseudohalides to form new carbon–carbon bonds. The phenolic hydroxyl group may be retained or protected depending on the synthetic strategy, while the chlorine substituent can provide an additional site for subsequent functionalization. Reaction optimization may be necessary because the neighboring hydroxyl group can influence the behavior and stability of the boronic acid functionality.
Applications in Medicinal Chemistry
In medicinal chemistry, (5-Chloro-2-hydroxyphenyl)boronic acid serves as a building block for preparing substituted aromatic compounds and investigating structure–activity relationships. The phenolic hydroxyl group can contribute to hydrogen-bonding interactions, while the chlorine substituent may influence electronic properties, lipophilicity, and molecular recognition. Researchers can incorporate this aromatic fragment into suitable candidate molecules to evaluate how these structural features affect physicochemical characteristics and biological activity.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring chlorinated and hydroxylated aromatic intermediates. Its boronic acid group provides a route for introducing a substituted phenyl fragment into more complex molecular frameworks through compatible coupling reactions. The hydroxyl group may also undergo suitable protection, etherification, or esterification reactions during multistep synthesis. These characteristics make the compound useful for developing structurally defined intermediates and exploring alternative synthetic pathways.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, (5-Chloro-2-hydroxyphenyl)boronic acid can be employed in specialty organic synthesis involving multifunctional aromatic building blocks. The presence of a phenolic hydroxyl group and a boronic acid functionality offers opportunities for selective chemical transformations and the preparation of more complex aromatic derivatives. Depending on the reaction conditions, the chlorine substituent may also support further functionalization, enabling the development of diverse molecular structures.
