The development of new energetic materials (explosives) can, e.g., lessen the environmental impact of their use or improve their performance. Advanced energetic materials often combine fuel and oxidizer in one molecule, e.g., by including NO₂ groups in addition to carbon. Nitrogen-rich azoles are often used as the basis of energetic materials, and they can undergo nitration at NH groups. However, relatively few 1,2,3-triazoles with N-nitro groups that can act as energetic materials are known.

Thomas M. Klapötke, Ludwig-Maximilian University of Munich, Germany, and colleagues have synthesized three high-energy 2-nitro-1,2,3-triazoles. First, the team prepared 4,5-bishydroxymethyl-1H-1,2,3-triazole via a [3+2]-cycloaddition of but-2-yne-1,4-diol and benzyl azide, followed by deprotection. A nitration with in-situ generated acetyl nitrate then gave 4,5-bis(nitratomethyl)-2-nitro-1,2,3-triazole (pictured). Similar energetic compounds with one or two azide groups were obtained via the nitration of the corresponding 1,2,3-triazole precursors.

The team found that the synthesized 4,5-bis(nitratomethyl)-2-nitro-1,2,3-triazole is a highly energetic material, with a high density, a high detonation velocity of 8590 ms^–1, and a high sensitivity to external stimuli.

• 4,5-Bisnitratomethyl and Similar Representatives of the Rare Class of 2-Nitro-1,2,3-triazoles,
  Maximilian Benz, Sabrina Dörrich, Thomas M. Klapötke, Tobias Lenz, Mohamed Mouzayek, Jörg Stierstorfer,
  Org. Lett. 2023.
  https://doi.org/10.1021/acs.orglett.3c02079