Propellants Explosives Pyrotechnics, Vol.44, No.7, 821-829, 2019
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 degrees 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).