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Procurement 2-Chloro-6-fluorophenylboronic acid丨CAS 313545-32-3
2-Chloro-6-fluorophenylboronic acid (CAS 313545-32-3) is a halogenated aromatic boronic acid featuring a chlorine atom at the 2-position and a fluorine atom at the 6-position of the benzene ring relative to the boronic acid functionality. This compound combines the synthetic versatility of an organoboron group with the electronic and steric characteristics of two different halogen substituents. It is a useful building block for medicinal chemistry, pharmaceutical intermediate development, organic synthesis, and specialty chemical research. The boronic acid functionality enables carbon–carbon bond formation through suitable cross-coupling reactions, while the chlorine and fluorine substituents provide defined structural features for molecular design.
Chemical Identifiers
| InChI | InChI=1S/C6H5BClFO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,10-11H |
| InChI Key | NXSZSZJWZVLHAY-UHFFFAOYSA-N |
| Smiles | B(C1=C(C=CC=C1Cl)F)(O)O |
| EC No. | 811-891-8 |
| MDL No. | MFCD04039892 |
| PubChem CID | 3549395 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Chloro-6-fluorophenylboronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare substituted biaryl compounds and other complex aromatic structures. Under appropriately selected palladium-catalyzed conditions, the boronic acid group can react with compatible organic halides or pseudohalides to form new carbon–carbon bonds. The chlorine and fluorine substituents may be retained in the resulting products when suitable reaction conditions are employed. Because both halogen atoms occupy positions adjacent to the boronic acid group, steric and electronic effects may influence reaction efficiency, making catalyst selection and process optimization important.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Chloro-6-fluorophenylboronic acid serves as a building block for preparing halogenated aromatic compounds and investigating structure–activity relationships. Fluorine substitution can influence molecular electronic properties, lipophilicity, and metabolic behavior, depending on the complete molecular structure. The chlorine substituent provides an additional structural feature that may affect molecular recognition and physicochemical characteristics. Researchers can incorporate this aromatic fragment into candidate molecules to evaluate how the 2-chloro-6-fluoro substitution pattern influences their properties and biological interactions.
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 practical route for introducing this aromatic fragment into more complex molecular frameworks through compatible cross-coupling reactions. Depending on the synthetic strategy, the chlorine substituent may also provide opportunities for subsequent functionalization under appropriately selected conditions. These characteristics make the compound useful for preparing structurally defined pharmaceutical research intermediates and exploring alternative synthetic pathways.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, 2-Chloro-6-fluorophenylboronic acid can be employed in specialty organic synthesis involving multifunctional aromatic building blocks. Its combination of a boronic acid group and two different halogen substituents supports the preparation of substituted biaryls, heteroaryl-containing compounds, and other complex organic molecules. Researchers may use it in molecular library development and synthetic methodology studies requiring controlled aromatic substitution and defined functional-group arrangements.
