1,3,5-Tris[(2H-tetrazol-5-yl)methyl]isocyanurate and Its Tricationic Salts as Thermostable and Insensitive Energetic Materials

Various energetic salts (3a–f) were obtained from 1,3,5-tris[(2H-tetrazol-5-yl)methyl]isocyanurate (3), while N2,N4,N6-tri(1H-tetrazol-5-yl)-1,3,5-triazine-2,4,6-triamine (5) and N,N′-{6-[(1H-tetrazol-5-yl)amino]-1,3,5-triazine-2,4-diyl}bis[N-(1H-tetrazol-5-yl)nitramide] (6) were obtained from cyanuric chloride via a simple, efficient two-step synthetic route from inexpensive starting materials. Compounds 3a–f and 6 show excellent detonation properties (VOD = 7876–8832 m s–1, and DP = 20.73–30.0 GPa), a high nitrogen content (>62%), and high positive heats of formation (205.2–1888.9 kJ mol–1) with excellent thermostability and remarkable insensitivity.