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(3,5-Difluorophenyl)boronic acid (CAS 156545-07-2), also known as 3,5-difluorobenzeneboronic acid, is a fluorinated aromatic organoboron compound featuring a boronic acid group and two fluorine substituents at the 3- and 5-positions of a benzene ring. Its symmetrical substitution pattern provides a well-defined aromatic building block with electron-withdrawing fluorine atoms. The boronic acid group enables carbon–carbon bond formation through suitable cross-coupling reactions, making this compound valuable for preparing fluorinated biaryl and heteroaromatic structures. It is primarily used in medicinal chemistry, pharmaceutical intermediate development, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H5BF2O2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,10-11H |
| InChI Key | QWQBQRYFWNIDOC-UHFFFAOYSA-N |
| Smiles | C1=C(C=C(F)C=C1F)B(O)O |
| EC No. | 605-060-7 |
| MDL No. | MFCD01318138 |
| PubChem CID | 2734338 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(3,5-Difluorophenyl)boronic acid is an organoboron coupling partner for Suzuki–Miyaura reactions. Under optimized palladium-catalyzed conditions, it can react with suitable aryl or heteroaryl halides to form carbon–carbon bonds. This transformation provides a practical route for introducing a 3,5-difluorophenyl fragment into complex aromatic molecules. The symmetrical fluorine substitution pattern allows researchers to prepare precisely substituted biaryl and heterobiaryl compounds without introducing additional regioisomeric possibilities within the difluorophenyl fragment.
Applications in Medicinal Chemistry
Fluorinated aromatic groups are frequently incorporated into medicinal chemistry research compounds because fluorine substitution can influence molecular lipophilicity, electronic properties, metabolic stability, and interactions with biological targets. (3,5-Difluorophenyl)boronic acid enables the introduction of a defined difluorophenyl group into candidate molecules through cross-coupling chemistry. Researchers may use this building block in lead optimization, analog preparation, and structure–activity relationship studies to evaluate the effects of fluorine substitution on molecular properties.
Applications in Pharmaceutical Intermediate Synthesis
This compound is useful for preparing pharmaceutical research intermediates containing fluorinated aromatic structures. Its boronic acid functionality allows the difluorophenyl group to be connected to various aromatic and heteroaromatic partners, supporting the construction of more complex molecular frameworks. The resulting intermediates may undergo additional functionalization depending on the target structure. The defined 3,5-difluoro substitution pattern is particularly useful when consistent electronic and structural characteristics are required across a series of related compounds.
Applications in Agrochemical Research
Fluorinated aromatic compounds are widely investigated in agrochemical development because fluorine atoms can modify physicochemical characteristics and influence interactions with biological targets. (3,5-Difluorophenyl)boronic acid may serve as an intermediate for preparing substituted aromatic compounds in exploratory crop protection research. Through suitable coupling reactions, researchers can incorporate the difluorophenyl fragment into candidate molecules and assess the effects of structural modification. Any herbicidal, fungicidal, or insecticidal activity depends on the complete molecular structure and requires experimental evaluation.
