A Facile and Versatile Synthesis of Energetic Furazan‐Functionalized 5‐Nitroimino‐1,2,4‐Triazoles

• Published in: Angewandte Chemie International Edition Vol. 56; no. 21; pp. 5877 - 5881
• Main Authors: Xu, Zhen, Cheng, Guangbin, Yang, Hongwei, Ju, Xuehai, Yin, Ping, Zhang, Jiaheng, Shreeve, Jean'ne M.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 15.05.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Chemistry; Chemistry, Multidisciplinary; density functional calculations; Detonation; energetic materials; heterocycles; Physical Sciences; Science & Technology; Sensitivity; structure elucidation; Thermal stability; Triazoles; X-ray diffraction; density functional calculations; DESIGN; heterocycles; HIGH-DENSITY; OXYGEN BALANCE; X-ray diffraction; SENSITIVITY; SURFACE ELECTROSTATIC POTENTIALS; energetic materials; structure elucidation; DERIVATIVES; SALTS
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201701659

An analogue‐oriented synthetic route for the formulation of furazan‐functionalized 5‐nitroimino‐1,2,4‐triazoles has been explored. The process was found to be straightforward, high yielding, and highly efficient, and scalable. Nine compounds were synthesized and the physicochemical and energetic properties, including density, thermal stability, and sensitivity, were investigated, as well as the energetic performance (e.g., detonation velocities and detonation pressures) as evaluated by using EXPLO5 code. Among the new materials, compounds 4–6 and 11 possess high densities, acceptable sensitivities, and good detonation performances, and thereby demonstrate the potential applications as new secondary explosives. High energy: An analogue‐oriented synthetic route for the formulation the title compounds was developed. The process was found to be straightforward, high yielding, and highly efficient, and scalable for the synthesis of high‐performance energetic materials.