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Selected (4-Chloro-2-methoxyphenyl)boronic acid丨CAS 762287-57-0
(4-Chloro-2-methoxyphenyl)boronic acid (CAS 762287-57-0) is a substituted aromatic boronic acid featuring a chlorine atom at the 4-position and a methoxy group at the 2-position of the benzene ring relative to the boronic acid functionality. This combination of organoboron, halogen, and ether functionalities makes the compound a useful building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty chemical research. Its boronic acid group supports carbon–carbon bond formation through suitable cross-coupling reactions, while the chlorine and methoxy substituents provide defined structural and electronic characteristics for molecular design.
Chemical Identifiers
| InChI | InChI=1S/C7H8BClO3/c1-12-7-4-5(9)2-3-6(7)8(10)11/h2-4,10-11H,1H3 |
| InChI Key | NZRRMTBNTSBIFH-UHFFFAOYSA-N |
| Smiles | COC1=C(C=CC(Cl)=C1)B(O)O |
| EC No. | 806-776-4 |
| MDL No. | MFCD02684317 |
| PubChem CID | 3858606 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(4-Chloro-2-methoxyphenyl)boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare substituted biaryl compounds and other aromatic structures. Under appropriate palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This enables the introduction of a 4-chloro-2-methoxyphenyl fragment into more complex molecular frameworks. The chlorine substituent may be retained for subsequent functionalization when suitable reaction conditions are selected, while the ortho-methoxy group may influence steric accessibility and coupling efficiency.
Applications in Medicinal Chemistry
In medicinal chemistry, (4-Chloro-2-methoxyphenyl)boronic acid serves as a building block for preparing substituted aromatic compounds and investigating structure–activity relationships. The chlorine atom can influence molecular lipophilicity, electronic properties, and interactions with biological targets, while the methoxy group introduces an ether functionality that may affect molecular polarity and hydrogen-bond acceptance. Researchers may incorporate this aromatic fragment into suitable candidate molecules to evaluate how the 4-chloro-2-methoxy substitution pattern influences physicochemical characteristics and biological activity.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring aromatic intermediates containing defined chlorine and methoxy substituents. Its boronic acid functionality provides a route for introducing the substituted phenyl fragment into more complex molecular structures through compatible coupling reactions. Depending on the synthetic strategy, the aromatic chlorine substituent may offer opportunities for additional functionalization, while the methoxy group can be retained or transformed under appropriate conditions. 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, (4-Chloro-2-methoxyphenyl)boronic acid can be employed in specialty organic synthesis involving multifunctional aromatic building blocks. The combination of a boronic acid group, chlorine substituent, and methoxy functionality supports the preparation of substituted biaryls, heteroaryl-containing compounds, and complex aromatic intermediates. Researchers may use it in molecular library development, synthetic methodology studies, and projects requiring controlled aromatic substitution patterns.
