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Top (4-Cyano-3-fluorophenyl)boronic acid丨CAS 843663-18-3
(4-Cyano-3-fluorophenyl)boronic acid (CAS 843663-18-3) is a multifunctional aromatic boronic acid featuring a cyano group at the 4-position and a fluorine atom at the 3-position of the benzene ring relative to the boronic acid functionality. Its combination of organoboron, nitrile, and aromatic fluorine functionalities makes it a useful building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty materials research. The boronic acid group supports carbon–carbon bond formation through suitable coupling reactions, while the cyano and fluorine substituents provide defined electronic and structural characteristics for molecular design.
Chemical Identifiers
| InChI |
InChI=1S/C7H5BFNO2/c9-7-3-6(8(11)12)2-1-5(7)4-10/h1-3,11-12H |
| InChI Key | DECWLXUOZUMPBF-UHFFFAOYSA-N |
| Smiles | B(C1=CC(=C(C=C1)C#N)F)(O)O |
| EC No. | 675-386-2 |
| MDL No. | MFCD03411549 |
| PubChem CID | 2783130 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(4-Cyano-3-fluorophenyl)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-cyano-3-fluorophenyl fragment into more complex molecular frameworks. The cyano and fluorine substituents may be retained in the resulting products when suitable reaction conditions are selected, providing useful structural features for subsequent research and synthetic modification.
Applications in Medicinal Chemistry
In medicinal chemistry, (4-Cyano-3-fluorophenyl)boronic acid serves as a building block for synthesizing fluorinated aromatic compounds and exploring structure–activity relationships. The cyano group introduces a strongly electron-withdrawing functionality that can influence molecular polarity and interactions with biological targets, while the fluorine substituent may affect electronic properties, lipophilicity, and metabolic behavior. Researchers may incorporate this aromatic fragment into suitable candidate molecules to investigate how the combination of nitrile and fluorine substitution affects physicochemical characteristics and biological activity.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a cyano- and fluoro-substituted aromatic framework. Its boronic acid functionality provides a route for introducing the substituted phenyl fragment into more complex molecules through compatible cross-coupling reactions. The nitrile group may also undergo selected chemical transformations, including hydrolysis or reduction, when appropriate conditions are employed. These characteristics make the compound useful for preparing structurally diverse pharmaceutical research intermediates and developing multistep synthetic pathways.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, (4-Cyano-3-fluorophenyl)boronic acid can be employed in specialty organic synthesis involving multifunctional aromatic building blocks. Its boronic acid group supports carbon–carbon bond formation, while the cyano and fluorine substituents provide additional structural features for molecular diversification. Researchers may use this compound in the preparation of substituted biaryls, heteroaryl-containing molecules, and other complex aromatic intermediates. The combination of different functional groups also makes it useful for investigating reaction selectivity and synthetic methodology.
