An Energetic (Nitro‐NNO‐azoxy)triazolo‐1,2,4‐triazine

7‐Nitro‐3‐(nitro‐NNO‐azoxy)[1,2,4]triazolo[5,1‐c][1,2,4]‐triazin‐4‐amine (4) is the first high‐melting compound bearing adjacent nitro‐NNO‐azoxy and amino groups. It was synthesized by nitration of 7‐nitro‐3‐(tert‐butyl‐NNO‐azoxy)[1,2,4]triazolo[5,1‐c][1,2,4]triazin‐4‐amine (3) with NO2BF4. Compound...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-07, Vol.2019 (26), p.4189-4195
Main Authors: Anikin, Oleg V., Leonov, Nikita E., Klenov, Michael S., Churakov, Aleksandr M., Voronin, Alexey A., Muravyev, Nikita V., Strelenko, Yurii A., Tartakovsky, Vladimir A.
Format: Article
Language:English
Subjects:
Azoxy compounds
Energetic materials
Heat of formation
Nitration
Nitrogen heterocycles
Thermal stability
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Summary:7‐Nitro‐3‐(nitro‐NNO‐azoxy)[1,2,4]triazolo[5,1‐c][1,2,4]‐triazin‐4‐amine (4) is the first high‐melting compound bearing adjacent nitro‐NNO‐azoxy and amino groups. It was synthesized by nitration of 7‐nitro‐3‐(tert‐butyl‐NNO‐azoxy)[1,2,4]triazolo[5,1‐c][1,2,4]triazin‐4‐amine (3) with NO2BF4. Compound 4 is a rather thermally stable (decomposition onset temperature 154 °C), highly energetic (calculated heat of formation 580 kcal·kg–1), and highly dense (1.875 g cm–3) material with a CO‐level oxygen balance. A method for the synthesis of a novel energetic compound, 7‐nitro‐3‐(nitro‐NNO‐azoxy)‐[1,2,4]triazolo[5,1‐c][1,2,4]triazin‐4‐amine, bearing adjacent nitro‐NNO‐azoxy and amine groups has been elaborated. It is a rather thermally stable (decomposition onset temperature 154 °C), highly energetic (calculated heat of formation 580 kcal·kg–1), and highly dense (1.875 g cm–3) material with a CO‐level oxygen balance.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900314