Synthesis of 2‑(3,5-Dinitrophenyl)-5-(trinitromethyl)-1,3,4-oxadiazole

• Published in: Journal of organic chemistry 2024-12, Vol.89 (23), p.17475-17481
• Main Authors: Chen, Yu-Cong, Yu, Qiong, Liu, Ning, Li, Tao, Yi, Wenbin
• Format: Article
• Language: English
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/acs.joc.4c02212

The trinitromethyl group plays a crucial role in the energetic material industry due to its high oxygen balance and energetic properties. This study focuses on the synthesis of dinitrophenyl-substituted trinitromethyl-1,3,4-oxadiazole. The introduction of dinitrophenyl groups to trinitromethyl-1,3,4-oxadiazole aims to improve its stability against heat-induced decomposition, a critical factor in ensuring the safe and reliable performance of energetic materials. Consequently, 2-(3,5-dinitrophenyl)-5-(trinitromethyl)-1,3,4-oxadiazole (6) was designed and synthesized. Compound 6 exhibited a remarkable thermal decomposition temperature of 117 °C, surpassing that of all other 1,3,4-oxadiazoles bearing the trinitromethyl group. This research highlights the incorporation of the dinitrophenyl ring to elevate the thermal decomposition temperature of the trinitromethyl group attached to the 1,3,4-oxadiazole ring, thereby presenting novel strategies for enhancing the thermal stability of these compounds.