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Scientific Supply 3-Cyano-4-fluorophenylboronic acid丨CAS 214210-21-6
3-Cyano-4-fluorophenylboronic acid (CAS 214210-21-6) is a multifunctional aromatic organoboron compound containing a boronic acid group, a cyano group at the 3-position, and a fluorine atom at the 4-position of a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the electronic characteristics of nitrile and fluorine substituents. The boronic acid functionality enables carbon–carbon bond formation, while the cyano group provides a useful synthetic handle for further chemical modification. These features make the compound a valuable building block for medicinal chemistry, pharmaceutical intermediate development, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C7H5BFNO2/c9-7-2-1-6(8(11)12)3-5(7)4-10/h1-3,11-12H |
| InChI Key | OLKIYJDSLMKNLC-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=C(F)C(C#N)=C1)O |
| EC No. | 675-057-3 |
| MDL No. | MFCD03095130 |
| PubChem CID | 2757964 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3-Cyano-4-fluorophenylboronic 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 to form new carbon–carbon bonds. This transformation enables the introduction of a 3-cyano-4-fluorophenyl fragment into more complex molecular structures. The nitrile and fluorine substituents may remain intact under suitable coupling conditions, allowing further functionalization of the resulting intermediates.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing fluorinated aromatic molecules containing nitrile functionality. Cyano groups are frequently investigated in pharmaceutical research because they can influence molecular polarity, electronic distribution, and interactions with biological targets. Fluorine substitution may further modify lipophilicity, metabolic behavior, and molecular recognition. Researchers can use 3-Cyano-4-fluorophenylboronic acid to prepare structurally diverse candidate compounds for lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
3-Cyano-4-fluorophenylboronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing both nitrile and fluorine substituents. The boronic acid group provides a route for connecting the substituted phenyl fragment to suitable aromatic or heteroaromatic coupling partners. The resulting nitrile-containing compounds may undergo further transformations, including hydrolysis to carboxylic acid derivatives or reduction to amines under appropriately selected conditions. This combination of functional groups supports flexible multistep synthesis and the preparation of advanced pharmaceutical research intermediates.
Applications in Agrochemical Research
Fluorinated aromatic nitriles are relevant to agrochemical research because their substituents can influence molecular stability, physicochemical properties, and biological interactions. 3-Cyano-4-fluorophenylboronic acid may serve as an intermediate for preparing substituted aromatic compounds investigated in crop protection research. Through suitable cross-coupling reactions, the compound can be incorporated into larger molecular frameworks, allowing researchers to evaluate different substitution patterns and their effects on chemical and biological properties.
