Synthesis and Characterization of the Energetic 3‐Azido‐5‐amino‐6‐nitro‐1,2,4‐triazine

Abstract

The reaction of diazotetrazole with nitroacetonitrile led to the isolation of the simple 1,2,4‐triazine‐based energetic 3‐azido‐5‐amino‐6‐nitro‐1,2,4‐triazine. It and related compounds were chemically characterized by NMR, IR, and single‐crystal X‐ray crystallography. Their energetic sensitivities (impact, friction) were experimentally determined and energetic performances calculated. The ability of 3‐azido‐5‐amino‐6‐nitro‐1,2,4‐triazine to form N‐oxides was also studied.

Synthesis and Properties of Lead‐Free Primary Explosive: Potassium 5‐(2,2‐Diamino‐1‐nitrovinyl)tetrazolate

“…Till now, energetic materials are playing vital roles in both military force and civil construction [1–7]. According to different functions and purposes, it can be divided into detonators, secondary explosives, and propellants [8–12].…”

Nitroacetonitrile as a versatile precursor in energetic materials synthesis

“…AANT was rst synthesized by Rusinov et al 48 in 1984 using free nitroacetonitrile. It was later synthesized in 2020 by Piercey et al 54 using the potassium salt of nitroacetonitrile and characterized, for the rst time, as an energetic. The commercial precursor 5-aminotetrazole was diazotized and reacted with the potassium salt of nitroacetonitrile (Scheme 16).…”

Energetic 1,2,4-Triazines: 3,5-Diamino-6-nitro-1,2,4-triazine and Its Oxide

“…Synthesis. The synthesis for DANT (Scheme 1) from 5amino-3-azido-6-nitro-1,2,4-triazine (AANT) 13 was based on a modified Staudinger reaction by reduction with triphenylphosphine. 14 AANT's reduction was screened in ethanol, methanol, 1-propanol and n-butanol and all led to simple reductions; so for all further attempts, ethanol was used as the solvent.…”

“…In the search for new insensitive energetic materials, we considered energetic 1,2,4-triazines due to the capability of its straightforward generation, especially when considering the ease of their synthesis when substituted with vicinal nitro groups. , 1,2,4-Triazines have been less studied as base energetic materials than other heterocyclic systems but still hold potential for high performance and good stability. The compound targeted for synthesis, 3,5-diamino-6-nitro-1,2,4-triazine (DANT), was previously identified by materials genome screening as a potentially insensitive material with high symmetry and planar geometry.…”