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

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 ( T p )=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 ( v D )=7878 m s −1 ] superior to that of 1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB).