Aromatic Nucleophilic Substitution via Chlorinated Nitrated Benzene Derivatives: Four Energetic Ring‐substituted Furazans

Abstract

According to an energetic molecule integration strategy, four energetic ring‐substituted furazans, 3‐amino‐4‐(2,4‐dinitroanilino)furazan (5), 3‐amino‐4‐picrylaminofurazan (6), 3,4‐bis(picrylamino)furazan (7) and 4‐(4‐aminofurazanamino)‐7‐nitro‐2,1,3‐benzoxadiazole (8), were synthesized through a similar aromatic nucleophilic substitution system. Crystal structures of 5–7 as well as that of a raw material 3,4‐diaminofurazan (1) for comparison are first reported and analyzed in detail. Thermal behavior, detonation properties and impact sensitivities of compounds 5–8 are discussed. Compounds 6–8 possess good potential to be used as energetic materials (EMs). Furthermore, compound 7, as the most promising high‐energy compound with high thermal stability and low sensitivity among the four ring‐substituted furazans, has the lowest impact sensitivity (>23.5 J) comparable to that of 1,1‐diamino‐2,2‐dinitroethylene (FOX‐7), the highest thermal stability [peak temperatures (Tp)=293.63 °C] close to that of cyclotetramethylene tetranitramine (HMX) and 2,4,6‐trinitrotoluene (TNT) and the best detonation performance [detonation pressure (P)=28.4 GPa and detonation velocity (vD)=7878 m s−1] superior to that of 1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB).