Regioselective introduction of 1,2,4-triazole into 1,2,3-triazole on N2-position with low sensitivity

Abstract Resolving the regioselectivity of N-position on nitrogen-rich heterocycles is an important task in the synthesis of high energy density materials (HEDMs). In this work we developed a simple two-step route to introduce 1,2,4-triazole into 4-nitro-1,2,3-triazole on N2-position, which shows excellent regioselectivity. The target compound 4-nitro-2-(1 H -1,2,4-triazol-3-yl)-1,2,3-triazole (3) was characterized by IR, multinuclear NMR, single crystal X-ray diffraction and DSC. Compound 3 exhibits a high thermal stability ( T m = 210 °C, T d = 230 °C). It also shows good detonation performances ( D v = 7094 m s −1 , P = 19.0 GPa) with low mechanical sensitivities ( FS > 360 N, IS > 20 N). As a result, compound 3 has a potential as a novel insensitive explosive.