1,2,4-Oxadiazole-derived polynitro energetic compounds with sensitivity reduced by a methylene bridge

Five energetic compounds bearing the framework of methylenebis-(1,2,4-oxadiazole-3-yl) are developed. All chemical structures were confirmed using infrared spectroscopy (IR), 1H NMR and 13C NMR spectroscopy, HRMS, and single crystal X-ray diffraction for pivotal intermediate diethyl 2,2′-(methylenebis(1,2,4-oxadiazole-3,5-diyl))diacetate (2) and diammonium salt 5. Bis(5-(trinitromethyl)-1,2,4-oxadiazol-3-yl)methane (3) showed high performance (D = 9053.2 m s−1, P = 37.4 GPa) and relatively low sensitivity (IS = 12.5 J, FS = 72 J). All the others are less sensitive than TNT.