4-Nitrophenylboronic Acid | CAS 24067-17-2 | ≥97%

Suzuki–Miyaura Cross-Coupling

• Strongly electron-deficient coupling partner for the synthesis of 4-nitrobiaryl and heteroaryl scaffolds via palladium catalysis — the para-nitro group is among the most powerful electron-withdrawing substituents in aromatic chemistry
• Distinctive electronic profile makes it complementary to electron-neutral and electron-rich boronic acids in systematic synthetic and mechanistic studies
• Compatible with ligand-free, aqueous, microwave-assisted, and heterogeneous palladium-catalysed Suzuki protocols

Nitro Group as Synthetic Handle

• The retained para-nitro group in coupling products provides a versatile handle for further elaboration — reduction to aniline, conversion to diazonium salt, or displacement in nucleophilic aromatic substitution
• Applied in the synthesis of nitroaromatic intermediates subsequently transformed to amino, hydroxy, or halogenated derivatives across pharmaceutical and agrochemical research
• Used in multi-step synthetic sequences where the nitro group serves as a masked amine or activating group for downstream functionalisation

Oxidative Ipso-Substitution & Phenol Synthesis

• Reagent for copper- and iron-catalysed oxidative hydroxylation reactions, enabling direct conversion of arylboronic acids to electron-poor phenols under mild aqueous conditions
• Applied in the preparation of 4-nitrophenol and related electron-deficient phenolic building blocks used in fine chemical synthesis

Boronate Esters & Iterative Synthesis

• Precursor for 4-nitrophenyl boronate esters (pinacol, MIDA, neopentyl glycol) used in iterative cross-coupling strategies and complex molecule assembly
• Applied in systematic Hammett substituent constant studies where the nitro group represents a strongly electron-withdrawing reference point on the σp scale