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Reliable Supplier 2,4-Bis(trifluoromethyl)phenylboronic acid丨CAS 153254-09-2
2,4-Bis(trifluoromethyl)phenylboronic acid (CAS 153254-09-2) is a fluorinated aromatic organoboron compound containing a boronic acid group and two trifluoromethyl substituents at the 2- and 4-positions of a benzene ring. The strongly electron-withdrawing trifluoromethyl groups influence the electronic properties, lipophilicity, and steric characteristics of the aromatic structure. This compound is a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, agrochemical research, and specialty fluorinated organic compounds.
Chemical Identifiers
| InChI | 1S/C8H5BF6O2/c10-7(11,12)4-1-2-6(9(16)17)5(3-4)8(13,14)15/h1-3,16-17H |
| InChI Key | WLYPBMBWKYALCG-UHFFFAOYSA-N |
| Smiles | OB(O)C1=CC=C(C=C1C(F)(F)F)C(F)(F)F |
| EC No. | 604-892-8 |
| MDL No. | MFCD01631349 |
| PubChem CID | 2782667 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2,4-Bis(trifluoromethyl)phenylboronic acid can serve as a coupling partner in Suzuki–Miyaura reactions for preparing fluorinated biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, its boronic acid group reacts with compatible aromatic halides to form new carbon–carbon bonds. The trifluoromethyl substituents remain incorporated into the resulting aromatic framework, enabling the preparation of highly fluorinated molecular structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 2,4-Bis(trifluoromethyl)phenylboronic acid provides a route for introducing a highly fluorinated phenyl fragment into candidate molecules. Trifluoromethyl substitution can influence molecular binding interactions, metabolic behavior, and membrane permeability, depending on the complete molecular structure. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to evaluate the effects of fluorination.
Applications in Pharmaceutical Intermediate Synthesis
This compound is useful for preparing fluorinated aromatic intermediates in pharmaceutical research. The two trifluoromethyl groups can influence molecular lipophilicity, electronic distribution, and physicochemical properties, while the boronic acid functionality supports the construction of complex aromatic frameworks. These characteristics make it relevant to the development of specialized pharmaceutical building blocks and fluorinated research compounds.
Applications in Agrochemical Research
Fluorinated aromatic compounds are important building blocks in agrochemical research because trifluoromethyl groups can modify molecular stability, lipophilicity, and biological interactions. 2,4-Bis(trifluoromethyl)phenylboronic acid may be used to synthesize substituted aromatic and heteroaromatic intermediates for exploratory crop protection programs. Its defined substitution pattern allows researchers to investigate the influence of multiple trifluoromethyl groups on molecular properties.
