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High Purity 4-(Trifluoromethoxy)phenylboronic acid丨CAS 139301-27-2
4-(Trifluoromethoxy)phenylboronic acid (CAS 139301-27-2), also known as 4-(trifluoromethoxy)benzeneboronic acid, is a fluorinated aromatic organoboron compound containing a boronic acid group and a trifluoromethoxy (-OCF₃) substituent at the para-position of a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the distinctive electronic and physicochemical characteristics of a trifluoromethoxy group. This compound is a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, agrochemical research, and specialty fluorinated organic compounds.
Chemical Identifiers
| InChI | 1S/C7H6BF3O3/c9-7(10,11)14-6-3-1-5(2-4-6)8(12)13/h1-4,12-13H |
| InChI Key | HUOFUOCSQCYFPW-UHFFFAOYSA-N |
| Smiles |
C1=C(OC(F)(F)F)C=CC(=C1)B(O)O |
| EC No. | 642-479-4 |
| MDL No. | MFCD01074648 |
| PubChem CID | 2734386 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-(Trifluoromethoxy)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 aromatic halides to form new carbon–carbon bonds. The trifluoromethoxy substituent can remain intact under appropriate conditions, enabling the introduction of a para-trifluoromethoxyphenyl fragment into complex molecular structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-(Trifluoromethoxy)phenylboronic acid provides a convenient route for incorporating a trifluoromethoxy-substituted phenyl group into candidate molecules. The -OCF₃ functionality is investigated because it can modify molecular lipophilicity, metabolic behavior, 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 trifluoromethoxy 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 aromatic frameworks, while the trifluoromethoxy group can influence lipophilicity, electronic distribution, and molecular interactions. These characteristics make it relevant to the development of specialized pharmaceutical intermediates and advanced organic compounds.
Applications in Agrochemical Research
4-(Trifluoromethoxy)phenylboronic acid may be used to prepare fluorinated aromatic compounds for agrochemical research. Trifluoromethoxy-substituted aromatic groups are relevant to crop protection chemistry because they can influence molecular stability, hydrophobicity, and biological interactions. The compound provides a useful intermediate for synthesizing specialized aromatic and heteroaromatic research compounds through suitable coupling reactions.
