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5-Chloro-2-methoxyphenylboronic acid丨CAS 89694-48-4 Supplier in China
5-Chloro-2-methoxyphenylboronic acid (CAS 89694-48-4), also known as (5-chloro-2-methoxyphenyl)boronic acid, is a substituted aromatic organoboron compound containing a boronic acid group, a chlorine atom at the 5-position, and a methoxy group at the 2-position of a benzene ring. Its structure combines the synthetic utility of an arylboronic acid with the electronic and steric characteristics of chloro and methoxy substituents. The boronic acid functionality enables carbon–carbon bond formation, while the chlorine and methoxy groups provide additional opportunities for structural modification. These features make the compound useful in medicinal chemistry, pharmaceutical intermediate synthesis, agrochemical research, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C7H8BClO3/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4,10-11H,1H3 |
| InChI Key | FMBVAOHFMSQDGT-UHFFFAOYSA-N |
| Smiles | COC1=CC=C(Cl)C=C1B(O)O |
| EC No. | 618-292-9 |
| MDL No. | MFCD01318966 |
| PubChem CID | 2735751 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
5-Chloro-2-methoxyphenylboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation introduces a 5-chloro-2-methoxyphenyl fragment into larger molecular frameworks. The ortho-methoxy group may influence coupling efficiency through steric effects, while the chlorine substituent can be retained under suitable chemoselective conditions for subsequent functionalization.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing chlorinated and methoxy-substituted aromatic research molecules. Chlorine substitution can influence molecular lipophilicity and electronic properties, while the methoxy group contributes hydrogen-bond acceptor functionality and affects molecular interactions. Through suitable coupling reactions, researchers can incorporate the substituted phenyl fragment into candidate compounds. These derivatives may be investigated in lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
5-Chloro-2-methoxyphenylboronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing both chlorine and methoxy substituents. Its boronic acid group provides a route for constructing carbon–carbon bonds with selected aromatic or heteroaromatic partners. The resulting intermediates can undergo further transformations depending on the target molecule. In suitable synthetic routes, the aryl chloride may participate in additional catalytic reactions, while the methoxy group can potentially be converted into a phenolic hydroxyl group under appropriate conditions.
Applications in Agrochemical Research
Chlorinated and methoxy-substituted aromatic compounds are relevant to agrochemical research because these functional groups can influence molecular stability, electronic characteristics, and interactions with biological targets. 5-Chloro-2-methoxyphenylboronic acid may serve as an intermediate for preparing substituted aromatic compounds investigated in crop protection research. Through cross-coupling and subsequent functionalization reactions, researchers can construct structurally diverse molecules for chemical and biological evaluation.
