CAS 86760-83-0, Cat. No EN300-7885583
Reagent for nitration
5-Methyl-1,4-dinitroimidazole (DNI) is a light-activated nitration reagent used for selective ortho-nitration of N-protected anilines under metal-free conditions1. It releases NO2 radicals under 390 nm LED irradiation, enabling efficient nitration without harsh acids. The reagent is compatible with Fmoc-, Ts-, and Boc-protected anilines, making it useful for peptide modifications2. It tolerates electron-withdrawing and electron-donating groups, including halides, nitro, and alkyl substituents. Bench-stable and non-volatile, it offers a safer alternative to traditional nitrating agents. This light-controlled method is mild, selective, and scalable, making it valuable for pharmaceutical and material chemistry.
Synonyms: 5-methyl-1,4-dinitro-1H-imidazole; DNI
Selected publications
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Photochemical Nitration of Protected Anilines by 5-Methyl-1,4-Dinitroimidazole.
Fan X.; Zhao Y.; Liu L.; Wang H. Chin J Chem 2023, 41 (13), 1589–1593. DOI: 10.1002/cjoc.202200725
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Photochemically-Induced Protein Tyrosine Nitration in Vitro and in Cellula by 5-Methyl-1,4-Dinitro-1H-Imidazole (DNI): Synthesis and Biochemical Characterization.
Rios N.; Aicardo A.; Chavarría C.; Ivagnes R.; Mastrogiovanni M.; Radi R.; Souza J. M. Free Radic Biol Med 2023, 209, 116–126. DOI: 10.1016/j.freeradbiomed.2023.09.038