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First Class (2-Fluoro-6-methoxyphenyl)boronic acid丨CAS 78495-63-3
(2-Fluoro-6-methoxyphenyl)boronic acid (CAS 78495-63-3), also known as 2-fluoro-6-methoxybenzeneboronic acid, is a substituted aromatic organoboron compound containing a boronic acid group and two different substituents at the adjacent 2- and 6-positions of a benzene ring. The fluorine atom modifies the electronic characteristics of the aromatic system, while the methoxy group contributes electron-donating and hydrogen-bond-accepting properties. This substitution pattern creates a sterically congested environment around the boronic acid group, making the compound a useful building block for preparing specialized aromatic structures in medicinal chemistry, pharmaceutical intermediate synthesis, and organic synthesis research.
Chemical Identifiers
| InChI | 1S/C7H8BFO3/c1-12-6-4-2-3-5(9)7(6)8(10)11/h2-4,10-11H,1H3 |
| InChI Key | XOVMDVZAWWQSDC-UHFFFAOYSA-N |
| Smiles | OB(C1=C(OC)C=CC=C1F)O |
| EC No. | 676-844-4 |
| MDL No. | MFCD02179483 |
| PubChem CID | 3294524 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(2-Fluoro-6-methoxyphenyl)boronic acid can serve as an organoboron coupling partner in Suzuki–Miyaura reactions. Under appropriately optimized palladium-catalyzed conditions, its boronic acid group can react with suitable aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation introduces a 2-fluoro-6-methoxyphenyl fragment into larger molecular frameworks. Because both positions adjacent to the boronic acid group are substituted, steric hindrance may affect coupling efficiency, making catalyst selection and reaction optimization particularly important.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound provides a route for incorporating a fluorinated, methoxy-substituted aromatic fragment into research molecules. Fluorine substitution can influence electronic properties, lipophilicity, and metabolic behavior, while the methoxy group may affect molecular polarity and interactions with biological targets. The 2,6-substitution pattern also creates a distinctive steric environment that can influence molecular conformation. These characteristics make the compound relevant to analog synthesis, lead optimization, and structure–activity relationship investigations.
Applications in Pharmaceutical Intermediate Synthesis
(2-Fluoro-6-methoxyphenyl)boronic acid may support pharmaceutical intermediate synthesis requiring highly substituted aromatic structures. Its boronic acid functionality enables the construction of biaryl and aryl–heteroaryl frameworks through suitable coupling reactions. The resulting intermediates retain the fluorine and methoxy substituents, providing opportunities for further molecular modification. Under appropriately selected conditions, the methoxy group may be converted into a phenolic hydroxyl group, allowing subsequent preparation of oxygen-functionalized derivatives.
Applications in Sterically Hindered Biaryl Synthesis
The presence of fluorine and methoxy substituents at both ortho-positions makes this compound particularly relevant to the synthesis of sterically hindered biaryl structures. After cross-coupling, these substituents can influence rotation around the newly formed aryl–aryl bond and affect the relative orientation of the aromatic rings. Researchers may investigate such compounds in studies involving conformational preferences, restricted rotation, and molecular structure–property relationships. Whether stable atropisomers form depends on the complete substitution pattern and rotational energy barrier.
