Synlett
DOI: 10.1055/a-2298-0282
letter

Introduction of an N-Amino Group onto 4-(Tetrazol-5-yl)-5-nitro-1,2,3-triazole: A Strategy for Enhancing the Density and Performance of Energetic Materials

Xun Huang
a   Key Laboratory of Fluorine and Nitrogen Chemistry and ­Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
,
Pinxu Zhao
a   Key Laboratory of Fluorine and Nitrogen Chemistry and ­Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
b   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei Road 200, Nanjing, 210094, Jiangsu, P. R. of China
,
Haifeng Huang∗
a   Key Laboratory of Fluorine and Nitrogen Chemistry and ­Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
,
Jun Yang∗
a   Key Laboratory of Fluorine and Nitrogen Chemistry and ­Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (NSFC) (Grant No. 22175196), the CAS Project for Young Scientists in Basic Research (Grant No.YSBR-052), the Shanghai Science and Technology Committee (20XD1404800) and the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB0590000).
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Abstract

2-Amino-5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (HANTT), its corresponding energetic salts and a dimeric azo compound are successfully synthesized. Compared to 5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (H2NTT), the neutral N-amino compound HANTT exhibits excellent properties in many aspects, including a higher density (ρ = 1.86 g cm–3), a better detonation performance (D v = 8931 m s–1, P = 32.2 GPa) and a higher thermal decomposition temperature (T d = 237 °C). Among the prepared materials, the hydroxylammonium energetic salt exhibits the best detonation performance (D v = 9096 m s–1, P = 32.8 GPa) and an acceptable mechanical sensitivity (IS = 12 J, FS = 144 N). HANTT, the energetic salts and the azo compound are fully characterized by infrared spectroscopy, multinuclear NMR spectroscopy, elemental analysis and differential scanning calorimetry.

Key words

energetic materials - 1,2,3-triazole - N-amino - hydrogen bond - detonation performance

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2298-0282.
  • Supporting Information


Publication History

Received: 27 February 2024

Accepted after revision: 02 April 2024

Accepted Manuscript online:
02 April 2024

Article published online:
24 April 2024

© 2024. Thieme. All rights reserved

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