N-Acetonitrile functionalized 3-nitrotriazole: Precursor to nitrogen rich stable and insensitive energetic materials

Abstract

In the field of energetic materials, prime attention has been given to the synthesis of environmentally compatible energetic materials having an adequate balance between energy and stability. For this purpose, nitrogen-rich heterocyclic rings have contributed as pivotal frameworks. Nitro-functionalized 1,2,4-triazoles have been profusely used as a constituent for synthesizing high-performing energetic materials (EMs) due to their high nitrogen content, good thermal stability, and modifiable sites via functionalization. Combination with a different energetic scaffold may provide an opportunity for accessible tailoring. In this work, in an effort to investigate the potential of 3-nitrotriazoles, its N-acetonitrile derivative 2 was synthesized, which was further converted to various explosophores. N-methylene-C bridged asymmetrically connected tetrazole (3) and 1,2,4-oxadiazole (9 and 10) based EMs have been synthesized. Further tuning of energetic properties via salt formation strategy was employed for the synthesis of compounds 4–7, 11 and 12. 1,2,4-oxadiazole-based compound 9 was also confirmed via X-ray diffraction analysis, and 10 was analyzed with ¹⁵N NMR spectroscopy. Compounds 3, 4, 5, 7 and 9 exhibited high thermal stabilities and were found to be insensitive towards impact and friction. Compounds 5, 6, and 10 exhibited detonation performance comparable to the conventional insensitive explosive TATB.