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Major Supplier 2-Chlorophenylboronic acid丨CAS 3900-89-8
2-Chlorophenylboronic acid (CAS 3900-89-8) is an aromatic organoboron compound featuring a boronic acid group and a chlorine substituent positioned adjacent to each other on a benzene ring. This ortho-substituted structure combines the versatile reactivity of the boronic acid functionality with a carbon–chlorine bond that can provide an additional site for chemical modification. It is widely useful as a building block in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions for preparing substituted biaryl compounds and more complex aromatic structures. The presence of both functional groups offers opportunities for sequential transformations and the development of structurally diverse molecules.
Chemical Identifiers
| InChI | 1S/C6H6BClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H |
| InChI Key | RRCMGJCFMJBHQC-UHFFFAOYSA-N |
| Smiles | ClC1=C(C=CC=C1)B(O)O |
| EC No. | 670-392-1 |
| MDL No. | MFCD00674012 |
| PubChem CID | 2734322 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
2-Chlorophenylboronic acid is a useful intermediate for preparing substituted biaryl compounds relevant to pharmaceutical research and medicinal chemistry. Through Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, its boronic acid group can be used to introduce the 2-chlorophenyl moiety into target molecular structures. The resulting compounds can serve as intermediates for further functionalization and support the preparation of research compounds and pharmaceutical building blocks. The ortho-chlorine substituent also provides a structural feature that can influence molecular conformation, steric effects, and subsequent reaction pathways.
Applications in Organic Synthesis and Cross-Coupling Reactions
A major application of 2-Chlorophenylboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. It reacts with suitable aryl or heteroaryl electrophiles to form carbon–carbon bonds, producing substituted biaryl compounds. The chlorine substituent may be retained during coupling under appropriately selected conditions, providing a potential handle for subsequent transformations. Depending on the catalyst and reaction system, chemists can explore sequential coupling strategies and other modifications to build more complex aromatic frameworks. This makes the compound useful in synthetic route development and the preparation of functionalized organic molecules.
Applications in Agrochemical and Fine Chemical Research
Substituted biaryl structures are found in a range of research compounds and specialty chemicals. 2-Chlorophenylboronic acid can support the synthesis of such structures by providing a defined chlorinated aromatic fragment. It may be used in the preparation of intermediates for agrochemical discovery, fine chemical development, and the synthesis of functional aromatic compounds. Its application depends on the target structure and the compatibility of the chlorine substituent with the selected reaction conditions.
Applications in Functional Materials Research
The 2-chlorophenyl group can be incorporated into extended aromatic structures investigated for their electronic, optical, and physicochemical properties. Through cross-coupling reactions, 2-Chlorophenylboronic acid provides a route to substituted biaryl compounds that may serve as intermediates in the development of organic functional materials, specialty polymers, and advanced molecular architectures. The chlorine substituent can also offer a site for further structural modification, depending on the chemistry employed.
