39512-81-7Relevant articles and documents
Synthesis and Characterization of the Potential Melt-Castable Explosive 3-(1,2,4-Oxadiazolyl)-5-Nitratomethyl Isoxazole
Byrd, Edward F. C.,Johnson, Eric C.,Miller, Christopher W.,Orlicki, Joshua A.,Reid, Tristen A.,Sabatini, Jesse J.,Sausa, Rosario C.
, p. 875 - 878 (2021/07/22)
The synthesis of 3-(1,2,4-oxadiazolyl)-5-nitratomethyl isoxazole (C6H4N4O5), its physical properties, and its theoretical performances are described. This energetic material was found to have a melting point range of 76.6–79.2 °C, and a thermal onset decomposition temperature of 184.5 °C. These thermal features put this material into the standalone melt-castable explosive class. The material was found to have TNT performance, and was found to be insensitive to impact, friction, and electrostatic discharge, despite having a nitric ester functionality. A critical reaction in making this molecule was the desymmetrization of diaminoglyoxime. The optimization of this transformation is described. Previous reports of this desymmetrization were found to be inaccurate, as the desymmetrization reaction produces a co-crystal of mono- and bi-1,2,4-oxadiazole products.
REARRANGEMENT OF 1-OXA-2-AZOLES. 3. REARRANGEMENT OF 1,2,4-OXADIAZOLE-3-CARBOXYLIC ACID AMIDOXIMES
Andrianov, V. G.,Semenikhina, V. G.,Eremeev, A. V.
, p. 646 - 650 (2007/10/02)
The rearrangement of unsubstituted 1,2,4-oxadiazole-3-carboxylic acid amidoxime and its N-isopropyl derivative to an aminofurazan is catalyzed by ammonia, while in the case of the amidoxime containing a piperidino substituent the rearrangement is catalyzed by acids.In ammonium hydroxide the piperidino and imidazolyl derivatives are converted to cyano amidoximes as a result of opening of the oxadiazole ring.
