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Major Supplier 3-(Trifluoromethyl)phenylboronic acid丨CAS 1423-26-3
3-(Trifluoromethyl)phenylboronic acid (CAS 1423-26-3) is an aromatic organoboron compound containing a boronic acid group and a trifluoromethyl (–CF₃) substituent at the meta position of a benzene ring. This molecular structure combines the synthetic versatility of boronic acid functionality with the distinctive electronic and physicochemical properties of a fluorinated aromatic group. It is a valuable building block in organic synthesis, particularly in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions for preparing trifluoromethyl-substituted biaryl compounds. Its defined meta-substitution pattern provides a useful structural feature for developing pharmaceutical intermediates, agrochemical research compounds, and functional aromatic molecules.
Chemical Identifiers
| InChI | 1S/C7H6BF3O2/c9-7(10,11)5-2-1-3-6(4-5)8(12)13/h1-4,12-13H |
| InChI Key | WOAORAPRPVIATR-UHFFFAOYSA-N |
| Smiles | FC(C1=CC(B(O)O)=CC=C1)(F)F |
| EC No. | 604-284-2 |
| MDL No. | MFCD00151854 |
| PubChem CID | 2734388 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
3-(Trifluoromethyl)phenylboronic acid is useful in medicinal chemistry for introducing a 3-trifluoromethylphenyl group into complex molecular structures. The trifluoromethyl group is frequently incorporated into pharmaceutical research compounds because it can influence lipophilicity, electron distribution, metabolic stability, and molecular interactions. Through suitable cross-coupling reactions with aryl or heteroaryl electrophiles, this compound enables the preparation of fluorinated biaryl intermediates for lead optimization, structure–activity relationship studies, and pharmaceutical compound development. The meta-positioned CF₃ group provides a defined substitution pattern for investigating how fluorinated aromatic fragments affect molecular properties.
Applications in Suzuki–Miyaura Cross-Coupling Reactions
One of the principal applications of 3-(Trifluoromethyl)phenylboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. Its boronic acid functionality can react with compatible aryl and heteroaryl halides or pseudohalides to form carbon–carbon bonds, providing access to trifluoromethyl-substituted biaryl structures. The CF₃ substituent is generally retained during appropriately selected coupling reactions, preserving its electronic and physicochemical characteristics in the resulting products. This transformation is widely used in synthetic chemistry to construct complex aromatic frameworks and diversify molecular structures.
Applications in Agrochemical and Fine Chemical Research
Trifluoromethyl-containing aromatic structures are important in agrochemical discovery and specialty chemical research. The CF₃ group can modify molecular lipophilicity, polarity, and chemical stability, making it a useful feature in the design of research compounds. 3-(Trifluoromethyl)phenylboronic acid provides a practical synthetic route for incorporating a meta-trifluoromethylphenyl fragment into larger molecular frameworks. Researchers can use it to prepare fluorinated intermediates and investigate their structural and physicochemical properties for potential applications in crop protection and fine chemical development.
Applications in Functional Materials Research
Fluorinated aromatic compounds are also investigated in the development of functional organic materials. Through suitable cross-coupling reactions, 3-(Trifluoromethyl)phenylboronic acid can be incorporated into extended aromatic structures with tailored electronic and physicochemical properties. The trifluoromethyl group may influence molecular polarity, intermolecular interactions, and thermal behavior, making the compound relevant to research involving specialty organic materials, advanced molecular architectures, and optoelectronic compounds.
