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Buy Bulk (2-Chloro-3-fluorophenyl)boronic acid丨CAS 871329-52-1
(2-Chloro-3-fluorophenyl)boronic acid (CAS 871329-52-1) is a halogen-substituted aromatic boronic acid containing a chlorine atom at the 2-position and a fluorine atom at the 3-position of the benzene ring relative to the boronic acid group. This compound combines the synthetic versatility of organoboron chemistry with the distinctive electronic and steric characteristics of chlorine and fluorine substituents. Its defined substitution pattern makes it a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, agrochemical research, and specialty organic chemistry. The boronic acid group enables carbon–carbon bond formation through suitable coupling reactions, while the two halogen substituents provide additional structural features for molecular design and functionalization.
Chemical Identifiers
| InChI | 1S/C6H5BClFO2/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,10-11H |
| InChI Key | TYOGIUGNZOBBHE-UHFFFAOYSA-N |
| Smiles | FC1=C(Cl)C(B(O)O)=CC=C1 |
| EC No. | 640-475-7 |
| MDL No. | MFCD07363741 |
| PubChem CID | 22309459 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(2-Chloro-3-fluorophenyl)boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, its boronic acid group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation allows the introduction of a 2-chloro-3-fluorophenyl fragment into more complex molecular frameworks. The chlorine and fluorine substituents may be retained during coupling when suitable reaction conditions are employed. Because the chlorine atom is located adjacent to the boronic acid group, steric effects may influence reaction efficiency and require careful optimization of the catalyst, solvent, and reaction conditions.
Applications in Medicinal Chemistry
In medicinal chemistry, (2-Chloro-3-fluorophenyl)boronic 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 to influence electronic properties, lipophilicity, molecular recognition, and metabolic behavior. The specific 2-chloro-3-fluoro substitution pattern provides a defined aromatic fragment for evaluating these effects. Researchers may use this compound in analog synthesis, lead optimization, and molecular library development to explore how the combination of chlorine and fluorine substitution affects candidate molecules.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a specifically substituted chlorofluorophenyl group. Its boronic acid functionality provides a route for connecting the aromatic fragment to compatible coupling partners through suitable carbon–carbon bond-forming reactions. The resulting products can serve as intermediates for further chemical modification or incorporation into more complex research molecules. Depending on the synthetic strategy, the aromatic chlorine substituent may provide an additional site for selected transformations, while the fluorine atom can influence the electronic characteristics of the final structure. These features make the compound useful for preparing structurally diverse pharmaceutical research intermediates.
Applications in Agrochemical Research
Halogenated aromatic structures are widely investigated in agrochemical chemistry because chlorine and fluorine substitution can influence physicochemical properties and interactions with biological targets. (2-Chloro-3-fluorophenyl)boronic acid may serve as an intermediate for preparing research compounds containing a 2-chloro-3-fluorophenyl structural unit. Through suitable coupling reactions, researchers can incorporate this fragment into larger molecular frameworks and evaluate the resulting compounds for relevant chemical and biological characteristics. Its potential applications include exploratory synthesis associated with crop protection research and specialty agrochemical intermediate development.
