The nitration of 1-methyl-2,4,5-triiodoimidazole and its oxidation by-product under nitration conditions

Abstract

ABSTRACT In this paper, 1-methyl-2,4,5-triiodoimidazole (1) was nitrified with various nitrating reagents. 1-Methyl-2,4,5-triiodoimidazole mononitrate (2), 2,4-diiodo-1-methyl-5-nitroimidzole (3), 2,5-diiodo-1-methyl-4-nitroimidzole (4), 4,5-dinitro-2-iodo-1-methylimidzole (5), 2,4-dinitro-5-iodo-1-methylimidzole (6) and 2,4-dinitro-1-methylimidzole (8) were obtained as intermediate derivatives; and 1-methyl-2,4,5-trinitroimidazole (7) was gave as target compound; meanwhile, 1-methylimidazolidine-2,4,5-trione (9) was formed as a nitration by-product. These compounds were characterized by melting point, IR, NMR, and elemental analysis. The structure of (2)–(6) and (9) were further confirmed by single crystal X-ray diffraction. Furthermore, the formation enthalpy, detonation velocity and detonation pressure of (3)–(8) were calculated, and thermal decomposition temperature, impact sensitivity and friction sensitivity were measured. Using this nitration strategy to nitrify dense iodine-rich compounds, Agent Defeat Weapons (ADWs) with balanced iodine content and energy can be obtained.