Synthesis and Properties of Thermostable Energetic Benzotriazines

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