Chemistry of Heterocyclic Compounds

, Volume 53, Issue 6–7, pp 737–739 | Cite as

Synthesis and Characterization of N 3 -(2,2,2-Trinitroethyl)-1,2,4-Oxadiazole-3,5-Diamine

  • David E. ChavezEmail author
  • Maxwell C. Schulze
  • Damon A. Parrish

The reaction of 1,2,4-oxadiazole-3,5-diamine with 2-fluoro-2,2-dinitroethanol or 2,2,2-trinitroethanol was studied. Only the 3-amino group was found to be reactive and underwent efficient Mannich-type condensation with 2,2,2-trinitroethanol, while only trace amounts of product from condensation with 2-fluoro-2,2-dinitroethanol were formed. N 3 -(2,2,2-Trinitroethyl)-1,2,4-oxadiazole-3,5-diamine was fully characterized, and its crystal structure and explosive sensitivity properties were determined. Calculated performance properties show that the product is a promising RDX-like material with a higher oxidizing potential.


2-fluoro-2,2-dinitroethanol 1,2,4-oxadiazole 2,2,2-trinitroethanol energetic materials Mannich reaction 


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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • David E. Chavez
    • 1
    Email author
  • Maxwell C. Schulze
    • 1
  • Damon A. Parrish
    • 2
  1. 1.Los AlamosUSA
  2. 2.WashingtonUSA

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