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Constructing Heat-Resistant and Insensitive Energetic Compounds with the Introduction of Cyano Group into Fused Pyrazolotriazine Skeleton

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journal contribution
posted on 15.12.2021, 13:36 authored by Zhen Cheng, Wei Yang, Qing Ma, Zhen-Qi Zhang, Lei Yang, Hongwei Yang, Gui-Juan Fan, Guangbin Cheng
Fused pyrazolotriazine frameworks have been used to develop novel heat-resistant energetic compounds. Diazotization of 3,4-diamino-4-nitropyrazole (1) and 3-anmio-4,5-dinitropyrazole (ADNP) followed by treatment with malononitrile afford compounds 2 and 3, including fused pyrazolotriazine ring surrounded by amino and cyano groups, respectively. Compounds 2 and 3 were thoroughly characterized by multinuclear NMR spectroscopy, infrared spectroscopy, and elemental analysis. The molecular structures of 2 and 3 were further confirmed by single crystal X-ray diffraction with the densities of 1.794 and 1.817 g·cm–3 (298 K), respectively. Moreover, compounds 2 and 3 have low impact and friction sensitivities (IS > 50 J, FS > 324 N). In particularly, compound 2 possesses the crossing stacking mode and high onset decomposition temperature of 370 °C, whose comprehensive performances are better than those of (2,2′,4,4′,6,6′-hexanitrostilbene) HNS and (2,6-bis­(picrylamino)-3,5-dinitropyridine) PYX. The efficient method of malononitrile cyclization provides a new idea for the development of novel heat-resistant energetic compounds.