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

Abstract 2-Amino-5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (HANTT), its corresponding energetic salts and a dimeric azo compound are 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, including a higher density (ρ = 1.86 g cm–3), a better detonation performance (D v = 8931 m s–1, P = 32.2 GPa) and a higher thermal decomposition temperature (T d = 237 °C). Among the prepared materials, the hydroxylammonium energetic salt exhibits the best detonation performance (D v = 9096 m s–1, P = 32.8 GPa) and an acceptable mechanical sensitivity (IS = 12 J, FS = 144 N). HANTT, the energetic salts and the azo compound are fully characterized by infrared spectroscopy, multinuclear NMR spectroscopy, elemental analysis and differential scanning calorimetry.