Enhancing energetic properties and sensitivity by incorporating amino and nitramino groups into a 1,2,4-oxadiazole building block

A single nitrogen-rich heterocyclic ring with many energetic groups is expected to exhibit excellent detonation performance. We report an effective approach for the synthesis of 3-amino-5-nitramino-1,2,4-oxadiazole, which has nitramino and amino groups in the same building block. The single-crystal X-ray structure shows layered hydrogen-bonding pairs as well as the presence of a water molecule which ensure insensitivity. Through incorporation of a cation, the hydrazinium or hydroxylammonium salts exhibit good energetic performance and acceptable sensitivities. Going with a bang: Hydrazinium 1,2,4-oxadiazolate combines amino and nitramino groups in a single heterocyclic ring and can be synthesized in a straightforward manner from inexpensive starting materials. Owing to its high performance and insensitivity, this compound may find practical use as an RDX replacement.