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Chemical Supplier (4-Fluoro-2-methoxyphenyl)boronic acid丨CAS 179899-07-1
(4-Fluoro-2-methoxyphenyl)boronic acid (CAS 179899-07-1), also known as 4-fluoro-2-methoxybenzeneboronic acid, is a substituted aromatic organoboron compound containing a boronic acid group, a fluorine atom at the 4-position, and a methoxy group at the 2-position of a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the electronic characteristics of fluorine and methoxy substituents. The boronic acid functionality enables carbon–carbon bond formation, while the fluorine and methoxy groups influence the electronic distribution and steric environment of the aromatic ring. These characteristics make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, agrochemical research, and specialty organic chemistry.
Chemical Identifiers
| InChI |
1S/C7H8BFO3/c1-12-7-4-5(9)2-3-6(7)8(10)11/h2-4,10-11H,1H3 |
| InChI Key |
ADJBXDCXYMCCAD-UHFFFAOYSA-N |
| Smiles |
OB(C1=CC=C(F)C=C1OC)O |
| EC No. | 690-489-2 |
| MDL No. | MFCD03788423 |
| PubChem CID | 2782672 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(4-Fluoro-2-methoxyphenyl)boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under 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 4-fluoro-2-methoxyphenyl fragment into more complex molecular structures. The ortho-methoxy group introduces steric effects near the boronic acid functionality, making reaction conditions and catalyst selection important considerations for efficient coupling.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing fluorinated and methoxy-substituted aromatic research molecules. Fluorine substitution can influence molecular lipophilicity, electronic properties, and metabolic behavior, while the methoxy group may contribute to molecular recognition and hydrogen-bond acceptor interactions. Through suitable cross-coupling reactions, researchers can incorporate the substituted phenyl fragment into candidate compounds. These derivatives may be investigated in lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
(4-Fluoro-2-methoxyphenyl)boronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing both fluorine and methoxy substituents. The boronic acid group provides a route for connecting the substituted phenyl fragment to aromatic or heteroaromatic coupling partners. The resulting intermediates may undergo additional chemical transformations depending on the target molecular structure. Under appropriately selected conditions, the methoxy group may also be converted into a phenolic hydroxyl group, providing further opportunities for molecular functionalization.
Applications in Agrochemical Research
Fluorinated aromatic compounds are widely investigated in agrochemical research because fluorine substitution can influence physicochemical properties and interactions with biological targets. (4-Fluoro-2-methoxyphenyl)boronic acid may serve as an intermediate for preparing substituted aromatic compounds used in exploratory crop protection research. Its combination of fluorine and methoxy groups provides a defined substitution pattern for evaluating structural effects. Through suitable coupling reactions, researchers can develop aromatic and heteroaromatic derivatives for further chemical and biological assessment.
