The nitration of 2,4,5-triiodoimidazole and its oxidation under nitration conditions

In this paper, the nitration of 2,4,5-trinitroimidazole (1) with nitric acid was reinvestigated. 2,5(4)-Diiodo-4(5)-nitroimidazole (2), 2,5(4)-dinitro-4(5)-iodoimidazole (3), 4,5-dinitro-2-iodoimidazole (11) and imidazolium 2,4,5-trinitroimidazole (12) were gave as nitration products, and ethanedioic acid (10) as oxidation by-product. All products were characterized using FT-IR, NMR and elemental analysis. Compounds (2), (10), (11), and (12) were further confirmed by single-crystal X-ray diffraction. (11) was an isomer of (3), which had not been reported in previous literatures, meanwhile (10) was obtained as an oxidation product instead of parabanic acid as report in the literature. Physicochemical properties of compounds (2), (3), (11), and (12) have been measured and calculated, which were compared with TNT. The detonation velocity, detonation pressure, impact sensitivity and friction sensitivity of (2), (3) and (11) were lower than TNT, however, explosive performance and impact sensitivity of (12) were greater than TNT.