4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 21, Pages 5877-5881

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701659

Keywords

density functional calculations; energetic materials; heterocycles; structure elucidation; X-ray diffraction

Funding

  1. Office of Naval Research [N00014-16-1-2089]
  2. Defense Threat Reduction Agency [HDTRA1-15-1-0028]
  3. National Natural Science Foundation of China [21376121, 21676147]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)

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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.

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