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Major Supplier 2-(Trifluoromethyl)benzeneboronic acid丨CAS 1423-27-4
2-(Trifluoromethyl)benzeneboronic acid (CAS 1423-27-4), also known as 2-(trifluoromethyl)phenylboronic acid, is an aromatic organoboron compound featuring a boronic acid group and a trifluoromethyl (–CF₃) substituent positioned adjacent to each other on a benzene ring. This structure combines the versatility of boronic acid chemistry with the distinctive electronic and physicochemical properties of a fluorinated aromatic group. It is a useful building block in organic synthesis, particularly in Suzuki–Miyaura cross-coupling reactions for preparing fluorinated biaryl compounds and other functionalized aromatic molecules. The ortho-substitution pattern also introduces steric and electronic effects that can influence molecular conformation and reaction behavior.
Chemical Identifiers
| InChI | 1S/C7H6BF3O2/c9-7(10,11)5-3-1-2-4-6(5)8(12)13/h1-4,12-13H |
| InChI Key | JNSBEPKGFVENFS-UHFFFAOYSA-N |
| Smiles | C1=CC=CC(=C1C(F)(F)F)B(O)O |
| EC No. | 640-203-7 |
| MDL No. | MFCD00236059 |
| PubChem CID | 2734387 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
2-(Trifluoromethyl)benzeneboronic acid is valuable in medicinal chemistry for introducing a 2-trifluoromethylphenyl group into complex molecular structures. The trifluoromethyl group is frequently incorporated into pharmaceutical research compounds because it can influence lipophilicity, metabolic stability, electron distribution, 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. Its ortho-substitution pattern also provides a useful structural feature for investigating steric effects in molecular design.
Applications in Suzuki–Miyaura Cross-Coupling Reactions
A principal application of 2-(Trifluoromethyl)benzeneboronic 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 group generally remains part of the product under appropriately selected coupling conditions, preserving its electronic and physicochemical influence. Because the boronic acid group is positioned adjacent to the bulky trifluoromethyl substituent, steric effects may need to be considered when selecting catalysts, ligands, bases, and reaction conditions.
Applications in Agrochemical and Fine Chemical Research
Trifluoromethyl-containing aromatic structures are widely explored in agrochemical discovery and specialty chemical development. The CF₃ group can modify molecular polarity, lipophilicity, and chemical stability, making it an important structural feature in the design of research compounds. 2-(Trifluoromethyl)benzeneboronic acid provides a synthetic route to incorporating this fluorinated aromatic fragment into larger molecular frameworks through suitable coupling reactions. It can support the preparation of fluorinated intermediates for evaluating molecular properties and potential applications in crop protection and fine chemical research.
Applications in Functional Materials Research
The combination of an aromatic ring and a strongly electron-withdrawing trifluoromethyl group makes this compound relevant to the preparation of specialized organic materials. Through cross-coupling reactions, it can be incorporated into extended aromatic structures investigated for their electronic, optical, and thermal properties. Fluorinated substituents may influence molecular polarity, intermolecular interactions, and material behavior, making this building block useful in the development of functional organic molecules and advanced materials.
