3-(3,5-Dinitrophenyl)-5-amino-1,2,4-oxadiazole: synthesis, structure and properties of a novel insensitive energetic material

The safety and thermal stability of energetic materials are of increasing concern, while simpler synthesis routes are also a major goal for researchers in the field of energetic materials. To meet these needs, a novel heat-resistant energetic compound 3-(3,5-dinitrophenyl)-5-amino-1,2,4-oxadiazole (3) with low mechanical sensitivity on the basis of combining dinitrobenzene and aminooxadiazole was synthesized through a simple method in this work. The structures of energetic intermediate 3-(3,5-dinitrophenyl)-5-(trichloromethyl)-1,2,4-oxadiazole (2) and 3 were characterized by NMR (¹H and ¹³C), infrared spectroscopy and X-ray crystallography. The results showed that both 2 and 3 are mechanically insensitive (IS > 60 J, FS > 360 N) and heat-resistant (T_d = 270 and 320 °C, respectively) with detonation properties (D = 6135 and 6396 m s⁻¹, P = 15.7 and 15.2 GPa) and both have relatively low melting points (T_m = 127 and 164 °C, respectively).