Synthesis and Crystal Structure of Bis-3,3'-(nitro-NNO-azoxy)-4,4'-azofurazan

During the recent decades, high-nitrogen heterocyclic compounds have been recognized as one class of promising energetic materials.[1][2][3] These energetic compounds with high nitrogen content have high heat of formation due to the large number of N-N and C-N bonds.4,5 A number of heterocyclebased energetic compounds were reported as potential materials for military and space applications.[6][7][8][9] Of these, furazan ring served as an efficient build-block.The combination of furazan ring with energetic substituents, such as amino (-NH 2 ), 10 nitro (-NO 2 ), 11,12 azide (-N 3 ) 13 and nitramine (-NHNO 2 ) 14 have been investigated.An unconventional explosophoric group, namely nitro-NNO-azoxy, through the destructive N-nitration of an X-NNO-azoxy compound (X=Ac, tBu) with nitronium was first reported by Churakov et al. 15 After that, Sheremetev A. B. et al. 16 synthesized bis-3,3'-(nitro-NNO-azoxy)-difurazanyl ether, which has high crystal density and excellent detonation properities.In this paper, a novel compound, bis-3,3'-(nitro-NNO-azoxy)-4,4'-azofurazan (BNOAF, 5), was designed and synthesized from 3,4-diaminofurazan (DAF, 1) via four steps, such as the reactions of oxidation, 17 condensation, 18 oxidation and nitrolysis (Scheme 1).The structure of title compound was confirmed by IR, 13 C NMR, 14 N NMR, MS and elemental analysis.The X-ray crystal structure of BNOAF was also studied.Furthermore, the performance of BNOAF was calculated.