4-Trifluoromethoxyphenylboronic Acid CAS 139301-27-2 | ≥98%

Suzuki–Miyaura cross-coupling reactions: 4-Trifluoromethoxyphenylboronic acid is widely used in palladium-catalysed Suzuki–Miyaura cross-coupling reactions for the introduction of the 4-(trifluoromethoxy)phenyl motif into organic molecules. The OCF₃ group is a metabolically stable bioisostere of methoxy, chloro, and trifluoromethyl groups, and its introduction via Suzuki coupling is one of the most reliable and scalable methods available. The compound couples with aryl halides, heteroaryl halides, and pseudohalides under standard Pd(0) catalysis conditions.

Synthesis of matrix metalloproteinase (MMP) inhibitors: This boronic acid has been used as a coupling partner in the synthesis of orally bioavailable matrix metalloproteinase inhibitors. The trifluoromethoxy substituent modulates the lipophilicity and metabolic stability of the resulting biaryl scaffold, which are critical parameters for oral bioavailability in structure–activity relationship studies.

DNA-dependent protein kinase (DNA-PK) inhibitors: The compound has been employed in the preparation of chromen-4-one-based inhibitors of DNA-dependent protein kinases, where the 4-(trifluoromethoxy)phenyl fragment is introduced via Suzuki coupling to the chromenone core.

Synthesis of lactate dehydrogenase inhibitors: 4-Trifluoromethoxyphenylboronic acid has been used as a reactant in the synthesis of lactate dehydrogenase inhibitors investigated for their effects on cancer cell proliferation, where the OCF₃-substituted aryl group contributes to target binding and pharmacokinetic properties.

PAI-1 inhibitor synthesis: The compound has been employed in the preparation of nitro-phenoxybenzoic acid derivatives designed as plasminogen activator inhibitor-1 (PAI-1) inhibitors, where the trifluoromethoxyphenyl unit is incorporated through cross-coupling chemistry.

Antituberculosis research: 4-Trifluoromethoxyphenylboronic acid has been used in the synthesis of PA-824 analogues, a class of nitroimidazooxazine compounds investigated as antituberculosis agents, where the OCF₃-aryl group is introduced to explore structure–activity relationships around the core scaffold.

Survival motor neuron (SMN) protein modulators: The compound has been used as a building block in the synthesis of modulators of survival motor neuron protein, which are investigated in the context of spinal muscular atrophy research.


Quorum sensing inhibition: 4-(Trifluoromethoxy)phenylboronic acid has been reported to inhibit autoinducer-2 (AI-2) quorum sensing in Vibrio harveyi, as documented by Ni et al. (Chem. Biol. Drug Des. 2009, 74, 51), demonstrating a direct biological activity of the boronic acid itself beyond its role as a synthetic intermediate.