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Hermann, Tobias S.; Karaghiosoff, Konstantin; Klapötke, Thomas M.; Stierstorfer, Jörg (2017): Synthesis and Characterization of 2,2 '-Dinitramino-5,5 '-bi(1-oxa-3,4-diazole) and Derivatives as Economic and Highly Dense Energetic Materials. In: Chemistry-A European Journal, Vol. 23, No. 50: pp. 12087-12091
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2,2'-Dinitramino-5,5'-bi(1-oxa-3,4-diazole) (2) is a new highly energetic material with superior calculated detonation performance in comparison to cyclo-1,3,5-trimethylene- 2,4,6-trinitramine (RDX) and penta-erythritoltetranitrate (PETN) and can be prepared by an economical and practical two-step synthesis. The starting material 2,2'-diamino-5,5'-bi(1-oxa-3,4-diazole) (1) is synthesized by the reaction of oxalyl dihydrazide with cyanogen bromide. Nitration of 1 yields the title compound in perfect yield and purity. The combination of its high density of 1.986 g cm(-3), the positive heat of formation (+190 kJ mol(-1)), and a slightly positive oxygen balance (+6.2%) results in ideal calculated detonation parameters (e.g. detonation velocity 9296 ms(-1)). The sensitivities toward impact and friction can be adjusted by deprotonation and formation of corresponding nitrogen-rich salts, for example, ammonium (3), hydroxylammonium (4), and guanidinium (5) salts.