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Large Volume (3-Chloro-2-methylphenyl)boronic acid丨CAS 313545-20-9
(3-Chloro-2-methylphenyl)boronic acid (CAS 313545-20-9) is a substituted aromatic boronic acid featuring a chlorine atom at the 3-position and a methyl group at the 2-position of the benzene ring relative to the boronic acid functionality. This combination of organoboron, halogen, and alkyl structural features makes it a useful building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty chemical research. The boronic acid group supports carbon–carbon bond formation through suitable coupling reactions, while the chlorine and methyl substituents provide defined electronic and steric characteristics for molecular design.
Chemical Identifiers
| InChI | InChI=1S/C7H8BClO2/c1-5-6(8(10)11)3-2-4-7(5)9/h2-4,10-11H,1H3 |
| InChI Key | BJPNVVXTUYMJPN-UHFFFAOYSA-N |
| Smiles | B(C1=C(C(=CC=C1)Cl)C)(O)O |
| EC No. | 640-272-3 |
| MDL No. | MFCD04115641 |
| PubChem CID | 3744103 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(3-Chloro-2-methylphenyl)boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to construct substituted biaryl compounds and other aromatic structures. Under suitable palladium-catalyzed conditions, the boronic acid group can react with compatible organic halides or pseudohalides to form new carbon–carbon bonds. The chlorine substituent may be retained in the resulting products when appropriate reaction conditions are selected, providing opportunities for further functionalization. The methyl group adjacent to the boronic acid functionality can influence steric accessibility, making catalyst selection and reaction optimization important for efficient coupling.
Applications in Medicinal Chemistry
In medicinal chemistry, (3-Chloro-2-methylphenyl)boronic acid serves as a building block for preparing substituted aromatic compounds and investigating structure–activity relationships. The chlorine atom may influence electronic properties, lipophilicity, and molecular interactions, while the methyl substituent introduces additional steric and hydrophobic characteristics. Researchers can incorporate this aromatic fragment into suitable candidate molecules to evaluate how the 3-chloro-2-methyl substitution pattern affects physicochemical properties and biological activity.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring aromatic intermediates with defined chlorine and methyl substituents. Its boronic acid functionality provides a route for introducing the substituted phenyl fragment into more complex molecular frameworks through compatible coupling reactions. Depending on the target structure and reaction conditions, the aromatic chlorine substituent may also offer opportunities for subsequent chemical transformations. These characteristics make the compound useful for preparing structurally diverse pharmaceutical research intermediates and exploring multistep synthetic pathways.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, (3-Chloro-2-methylphenyl)boronic acid can be employed in specialty organic synthesis involving multifunctional aromatic building blocks. Its combination of a boronic acid group, chlorine substituent, and methyl group enables the preparation of substituted biaryls, heteroaryl-containing compounds, and other complex organic molecules. The compound may support molecular library development and synthetic methodology research where controlled aromatic substitution and functional-group compatibility are important.
