1,3,5-Tris[(2 H -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[(2 H -tetrazol-5-yl)methyl]isocyanurate ( 3 ), while N2,N4,N6-tri(1 H -tetrazol-5-yl)-1,3,5-triazine-2,4,6-triamine ( 5 ) and N , N '-{6-[(1 H -tetrazol-5-yl)amino]-1,3,5-triazine-2,4-diyl}bis[ N -(1 H -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.