Azido and Tetrazolo 1,2,4,5-Tetrazine N-Oxides

David E. Chavez, Damon A. Parrish, Lauren Mitchell, Greg H. Imler

Research output: Contribution to journalArticlepeer-review

120 Scopus citations


This study presents the synthesis and characterization of the oxidation products of 3,6-diazido-1,2,4,5-tetrazine (1) and 6-amino-[1,5-b]tetrazolo-1,2,4,5-tetrazine (2). 3,6-Diazido-1,2,4,5-tetrazine-1,4-dioxide was produced from oxidation with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to two different products, 6-amino-[1,5-b]tetrazolo-1,2,4,5-tetrazine mono-N-oxide and di-N-oxide. These N-oxide compounds display promising performance properties as energetic materials.

Original languageEnglish (US)
Pages (from-to)3575-3578
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number13
StatePublished - Mar 20 2017

Bibliographical note

Funding Information:
We would like to thank the Joint Munitions Technology Development Program and The Laboratory Directed Research and Development Program for funding this work. Los Alamos National Laboratory is operated by Los Alamos National Security (LANS, LLC) under contract No. DE-AC52-06NA25396 for the U.S. Department of Energy. We also thank the Office of Naval Research (Award No. N00014-15-WX-0-0149) for funding this work. We would like to thank Stephanie Hagelberg (elemental analysis) for characterization, and Hongzhao Tian and Mary Sandstrom for thermal analysis and sensitivity testing.

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim


  • 1,2,4,5-tetrazine
  • N-oxides
  • azides
  • energetic materials
  • tetrazole


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