Introduction of the N-amino group into 4-(tetrazol-5-yl)-5-nitro-1,2,3-triazole: a strategy for enhancing density and performance of energetic materials

2-Amino-5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (4, HANTT), its energetic salts 5-7 and the azo compound 8 were successfully synthesized. Compared to 5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (H2NTT), the neutral N-amino compound HANTT exhibits excellent properties in many aspects, such as higher density (ρ = 1.86 g cm–3), better detonation performance (Dv = 8931 m s–1, P = 32.2 GPa) and higher thermal decomposition temperature (Td = 237 oC). Among them, the hydroxylammonium salt 6 exhibited the best detonation performance (Dv = 9096 m s–1, P = 32.8 GPa) and the acceptable mechanical sensitivity (IS = 12 J, FS = 144 N). All these compounds 4-8 were fully characterized by infrared spectroscopy, multinuclear NMR spectroscopies, elemental analysis and differential scanning calorimetry.