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Bulk Inquiry 4-(Trifluoromethyl)phenylboronic acid丨CAS 128796-39-4
4-(Trifluoromethyl)phenylboronic acid (CAS 128796-39-4), also known as 4-(trifluoromethyl)benzeneboronic acid, is a fluorinated aromatic organoboron compound containing a boronic acid group and a trifluoromethyl (-CF₃) substituent at the para-position of a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the strong electron-withdrawing properties of a trifluoromethyl group. This compound is a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, agrochemical research, and specialty fluorinated organic chemistry.
Chemical Identifiers
| InChI | 1S/C7H6BF3O2/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4,12-13H |
| InChI Key | ALMFIOZYDASRRC-UHFFFAOYSA-N |
| Smiles | FC(C1=CC=C(B(O)O)C=C1)(F)F |
| EC No. | 603-301-0 |
| MDL No. | MFCD00151855 |
| PubChem CID | 2734389 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-(Trifluoromethyl)phenylboronic acid is a useful coupling partner in Suzuki–Miyaura reactions for preparing fluorinated biaryl and aryl–heteroaryl compounds. Under suitable palladium-catalyzed conditions, its boronic acid group reacts with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. The trifluoromethyl substituent generally remains intact, enabling the introduction of a para-trifluoromethylphenyl fragment into complex aromatic structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-(Trifluoromethyl)phenylboronic acid provides a convenient route for incorporating a trifluoromethyl-substituted phenyl group into candidate molecules. The -CF₃ functionality is frequently investigated because it can influence metabolic stability, molecular lipophilicity, and interactions with biological targets. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to evaluate the effects of trifluoromethyl substitution.
Applications in Pharmaceutical Intermediate Synthesis
This compound serves as a building block for preparing fluorinated aromatic intermediates used in pharmaceutical research. Its boronic acid functionality supports the construction of complex molecular frameworks, while the trifluoromethyl group can influence lipophilicity, electronic distribution, and molecular interactions. These characteristics make it relevant to the development of specialized pharmaceutical intermediates and structurally diverse research compounds.
Applications in Agrochemical Research
4-(Trifluoromethyl)phenylboronic acid may be used to prepare fluorinated aromatic compounds for agrochemical research. Trifluoromethyl-substituted phenyl groups are relevant to crop protection chemistry because they can modify physicochemical properties and biological interactions. The compound provides a useful intermediate for synthesizing specialized aromatic and heteroaromatic structures in exploratory agrochemical development.
