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High Quality 2-Chloro-6-methoxyphenylboronic acid丨CAS 385370-80-9
2-Chloro-6-methoxyphenylboronic acid (CAS 385370-80-9) is a substituted aromatic boronic acid containing a chlorine atom at the 2-position and a methoxy group at the 6-position of the benzene ring, relative to the boronic acid functionality. The combination of organoboron, halogen, and ether functionalities makes this compound a useful building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty chemical research. Its boronic acid group provides a reactive site for carbon–carbon bond formation, while the chlorine and methoxy substituents offer additional structural features for molecular design and synthetic diversification.
Chemical Identifiers
| InChI | InChI=1S/C7H8BClO3/c1-12-6-4-2-3-5(9)7(6)8(10)11/h2-4,10-11H,1H3 |
| InChI Key | XNWCIDBPLDKKAG-UHFFFAOYSA-N |
| Smiles | B(C1=C(C=CC=C1Cl)OC)(O)O |
| EC No. | |
| MDL No. | MFCD04039878 |
| PubChem CID | 3378271 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Chloro-6-methoxyphenylboronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare substituted biaryl compounds and other aromatic structures. Under suitable palladium-catalyzed conditions, the boronic acid functionality can react with compatible organic halides or pseudohalides to form new carbon–carbon bonds. The chlorine and methoxy substituents can be retained in the resulting products when appropriate reaction conditions are selected. Because both substituents are located adjacent to the boronic acid group, steric effects may influence coupling efficiency, making catalyst selection and reaction optimization important.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Chloro-6-methoxyphenylboronic acid serves as a building block for preparing substituted aromatic compounds and investigating structure–activity relationships. The chlorine substituent may influence electronic characteristics, lipophilicity, and molecular interactions, while the methoxy group introduces an ether functionality that can affect steric and electronic properties. Researchers can incorporate this aromatic fragment into suitable candidate molecules to explore how the 2-chloro-6-methoxy substitution pattern affects physicochemical characteristics and biological activity.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring aromatic intermediates with defined chlorine and methoxy substituents. Its boronic acid functionality provides a convenient synthetic route for introducing the substituted phenyl fragment into more complex molecular frameworks. Depending on the target structure and reaction conditions, the chlorine substituent may also provide opportunities for subsequent functionalization. These features make the compound useful for preparing structurally diverse pharmaceutical research intermediates and exploring multistep synthetic strategies.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, 2-Chloro-6-methoxyphenylboronic acid can be employed in specialty organic synthesis involving multifunctional aromatic building blocks. Its combination of a boronic acid group, aromatic chlorine substituent, and methoxy functionality supports the preparation of substituted biaryls, heteroaryl-containing compounds, and other complex organic molecules. The compound may be used in molecular library development and synthetic methodology research where controlled aromatic substitution is required.
