An Energetic Triazolo‐1,2,4‐Triazine and its N‐Oxide

The reaction of 3‐amino‐5‐nitro‐1,2,4‐triazole with nitrous acid produces the corresponding diazonium salt. When the diazonium salt is treated with nitroacetonitrile, a subsequent condensation and cyclization reaction occurres to produced 4‐amino‐3,7‐dinitrotriazolo‐[5,1‐ c ][1,2,4] triazine (DPX‐26). X‐ray crystallographic analysis shows that the DPX‐26 has a density of 1.86 g cm −3 , while it is calculated to have a heat of formation of 398.3 kJ mol −1 . DPX‐26 is predicted to approach the explosive performance of RDX but displays significantly better safety properties. Oxidation of DPX‐26 using hypofluorous acid produces 4‐amino‐3,7‐dinitrotriazolo‐[5,1‐ c ][1,2,4] triazine 4‐oxide (DPX‐27), which is also predicted to be a high‐performance material with enhanced safety properties.