Synthesis and Properties of Thermostable Energetic Benzotriazines

In an effort to balance energy and molecular stability effectively, several energetic compounds (3–6) based on benzotriazine were designed and synthesized. These structures were comprehensively characterized using NMR, IR, and elemental analysis, with compounds 3, 5, and 6 further confirmed by single-crystal X-ray diffraction. Notably, 3-amino-5,7-dinitrobenzo[e][1,2,4]triazine 1-oxide (5), which features a face-to-face crystal stacking arrangement, exhibits good detonation velocity (D_v = 8050 m/s), a high thermal decomposition temperature (T_d = 290 °C), and low sensitivities (impact sensitivity >40 J, friction sensitivity >360 N). The preparation of compound 5 was further optimized by using a commercially available flow microreactor system, achieving an improved yield of 62%. Overall, the comprehensive properties of compound 5 make it a promising candidate for heat-resistant explosive applications.