The synthesis, property and reduction of high-nitrogen compound 3,3′,5,5′-tetraazido-4,4′-bis(1,2,4-triazole)

High-nitrogen compound, 3,3′,5,5′-tetraazido-4,4′-bis(1,2,4-triazole) (TABT, 83.99% N), is synthesized from sodium azide and 3,3′,5,5′-tetrabromo-4,4′-bis(1,2,4-triazole) (TBBT) which is prepared by the bromination of 4,4′-bis(1,2,4-triazole) (BTz). It is fully characterized by IR, HRMS, NMR, and single crystal X-ray diffraction showing two triazole rings of TABT perpendicular to each other. DSC and TGA are employed to study TABT’s thermal stability with a decomposition temperature at 125.39 °C (onset). The calculated detonation heat of TABT and the predicted detonation velocity are 6449 kJ·kg−1 and 8649 m·s−1, respectively. The reduction of TABT with hydrogen and Pd/C gave the stabilized 3,3′,5,5′-tetra(t-butyloxycarbamido)-4,4′-bis(1,2,4-triazole) (11) in the presence of (Boc)2O, providing an alternative path to the high energy density material (HDEM) TNBT [3,3′,5,5′-tetranitro-4,4′-bis(1,2,4-triazole)].