Versatile functionalization of 3,5-diamino-4-nitropyrazole for promising insensitive energetic compounds

Variation of functional groups offers an efficient approach for tuning properties of materials such as thermal stability, and detonation performance while improving sensitivities to mechanical stimuli. Now versatile functionalization of 3,5-diamino-4-nitropyrazole involving the introduction of a tetrazole ring, or a guanyl group, or ring expansion is described. All of the compounds were fully characterized and some of them (2, 9 and 13) were verified by single crystal X-ray diffraction. Based on their good thermal stabilities and high detonation performance as well as insensitive properties, they are potentially insensitive energetic compounds.