High-Nitrogen Materials Derived from 5-Nitromethyl-1H-tetrazole

This work outlines the synthesis of 5-nitromethyl-1H-tetrazole (NMT) and its use in the synthesis of various high-nitrogen materials. It can be reacted with the diazonium salt of 5-aminotetrazole to produce a tetrazene-like energetic hydrazone material. Like tetrazene, N-(1H-tetrazole-5-yl)nitro(1H-tetrazole-5-yl)hydrazone hydrate (TNTH) exhibits high sensitivity to mechanical stimuli while being more thermally stable: 209 °C decomposition and 16% mass loss at 90 °C for 10,000 min versus 150 °C decomposition and 36% mass loss for tetrazene. NMT can also be used as an activated methylene carbon source in the synthesis of 2,3,5-trisubstituted tetrazolium salts. 2,3,5-Tri(1H-tetrazole-5-yl)-2H-tetrazole as an internal zwitterion (TTT) was synthesized and found to be deliquescent, and its salts were extremely unstable.

5-Nitromethyl-1H-tetrazole (NMT) is a versatile reagent for the synthesis of high-nitrogen content materials. It shows promise as an activated methylene carbon source for the synthesis of 2,3,5-substituted tetrazolium salts and hydrazones with high-nitrogen heterocycle substitution.