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Main Supplier 4-Chlorophenylboronic acid丨CAS 1679-18-1
4-Chlorophenylboronic acid (CAS 1679-18-1) is an aromatic organoboron compound featuring a boronic acid group and a chlorine atom positioned para to each other on a benzene ring. This combination of functional groups makes it a versatile building block in organic synthesis, particularly in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. The boronic acid functionality enables carbon–carbon bond formation with suitable aryl and heteroaryl electrophiles, while the chlorine substituent can remain in the resulting molecule as a potential site for further chemical modification. Its defined molecular structure makes it valuable for preparing substituted biaryl compounds, pharmaceutical intermediates, and functional aromatic materials.
Chemical Identifiers
| InChI | 1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H |
| InChI Key | CAYQIZIAYYNFCS-UHFFFAOYSA-N |
| Smiles | ClC1=CC=C(B(O)O)C=C1 |
| EC No. | 216-845-5 |
| MDL No. | MFCD00039137 |
| PubChem CID | 74299 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
4-Chlorophenylboronic acid is useful in medicinal chemistry for introducing a 4-chlorophenyl group into complex molecular structures. Through suitable Suzuki–Miyaura coupling reactions, it can be combined with aryl or heteroaryl halides to produce chlorinated biaryl compounds and related intermediates. Chlorine substitution can influence molecular size, lipophilicity, electronic properties, and metabolic behavior, making chlorinated aromatic fragments useful in structure–activity relationship studies and lead optimization. The resulting compounds may serve as intermediates in pharmaceutical research and the development of structurally diverse candidate molecules.
Applications in Suzuki–Miyaura Cross-Coupling Reactions
One of the principal applications of 4-Chlorophenylboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. Its boronic acid group reacts with compatible aryl or heteroaryl halides and pseudohalides to form carbon–carbon bonds, providing an efficient route to substituted biaryl structures. The para-chlorine substituent is often retained under appropriately selected coupling conditions, allowing further functionalization through suitable transformations of the carbon–chlorine bond. This provides flexibility for sequential synthesis and the preparation of more complex aromatic compounds.
Applications in Agrochemical and Fine Chemical Research
Chlorinated aromatic structures are important building blocks in the synthesis of various specialty chemicals and agrochemical research compounds. 4-Chlorophenylboronic acid provides a convenient route to incorporating a para-chlorophenyl fragment into larger molecular frameworks. Researchers can use it to prepare substituted aromatic intermediates and investigate how chlorine substitution affects molecular properties and chemical performance. Its suitability for a particular application depends on the target structure and the compatibility of the selected reaction conditions.
Applications in Functional Materials Research
The 4-chlorophenyl group can be incorporated into extended aromatic structures investigated for their electronic, optical, and thermal properties. Through cross-coupling reactions, 4-Chlorophenylboronic acid can contribute to the synthesis of substituted biphenyls and other aromatic compounds used in functional materials research. The chlorine substituent may also provide an additional handle for molecular modification, enabling the preparation of derivatives with different structural and physicochemical characteristics.
