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2-Chloro-4-fluorobenzeneboronic acid (CAS 313545-72-1), also known as 2-chloro-4-fluorophenylboronic acid, is a halogenated aromatic organoboron compound featuring a chlorine atom at the 2-position, a fluorine atom at the 4-position, and a boronic acid group attached to the benzene ring. This compound combines the synthetic versatility of an arylboronic acid with the electronic and structural characteristics of a chlorofluorinated aromatic framework. The chlorine substituent introduces steric and electronic effects near the boronic acid group, while the fluorine substituent influences the electronic distribution and physicochemical characteristics of the aromatic ring. These features make 2-Chloro-4-fluorobenzeneboronic acid a useful building block for medicinal chemistry, pharmaceutical intermediate development, agrochemical research, Suzuki–Miyaura cross-coupling chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H5BClFO2/c8-6-3-4(9)1-2-5(6)7(10)11/h1-3,10-11H |
| InChI Key | XOFNMNLYGPKKOV-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=C(F)C=C1Cl)O |
| EC No. | 639-419-4 |
| MDL No. | MFCD02684295 |
| PubChem CID | 17750229 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Chloro-4-fluorobenzeneboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation enables the introduction of a 2-chloro-4-fluorophenyl fragment into more complex molecular frameworks. The chlorine and fluorine substituents may remain intact under suitably selective reaction conditions, providing opportunities for subsequent molecular modification. Because the chlorine atom is 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-4-fluorobenzeneboronic acid serves as a building block for preparing halogenated aromatic compounds and investigating structure–activity relationships. Chlorine and fluorine substituents are frequently incorporated into pharmaceutical research molecules because they can influence electronic distribution, lipophilicity, molecular conformation, and interactions with biological targets. The boronic acid functionality provides a route for introducing the 2-chloro-4-fluorophenyl fragment into structurally diverse candidate molecules. Researchers may use this compound in lead optimization, analog synthesis, and compound library development to evaluate how specific halogen substitution patterns affect molecular properties.
Applications in Pharmaceutical Intermediate Synthesis
2-Chloro-4-fluorobenzeneboronic acid may support pharmaceutical research programs requiring intermediates containing a chlorofluorinated aromatic structural unit. Through suitable cross-coupling reactions, the compound can be connected to compatible aromatic or heteroaromatic partners to produce more complex molecular frameworks. The resulting compounds may undergo additional transformations depending on the desired target structure. The chlorine substituent provides a potential site for selected transition-metal-catalyzed reactions, while the fluorine substituent contributes distinctive electronic characteristics. This combination of functional groups supports the development of multistep synthetic routes and the preparation of advanced pharmaceutical research intermediates.
Applications in Agrochemical Research
Halogenated aromatic compounds are widely investigated in agrochemical chemistry because chlorine and fluorine substituents can influence physicochemical properties and interactions with biological targets. 2-Chloro-4-fluorobenzeneboronic acid may serve as an intermediate for preparing research compounds containing a chlorofluorinated phenyl fragment. Through suitable coupling and functionalization reactions, researchers can incorporate this structural unit into larger aromatic or heteroaromatic frameworks. The resulting compounds may be evaluated for chemical characteristics and potential biological activity in exploratory crop protection research. Their practical suitability depends on the molecular structure and performance of the final compounds.
