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Mendeleev Communications, 2010, Volume 20, Issue 5, Pages 253–254
DOI: https://doi.org/10.1016/j.mencom.2010.09.003
(Mi mendc3055)
 

This article is cited in 49 scientific papers (total in 49 papers)

The specific reactivity of 3,4,5-trinitro-1H-pyrazole

I. L. Dalinger, I. A. Vatsadze, T. K. Shkineva, G. P. Popova, S. A. Shevelev

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: Nitration of 3,5-dinitropyrazole with HNO3–H2SO4 mixture gives 3,4,5-trinitro-1H-pyrazole, which in reaction with ammonia, amines or thiols under mild conditions undergoes regioselective nucleophilic substitution of the 4-positioned nitro group.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (68.3 Kb)


Citation: I. L. Dalinger, I. A. Vatsadze, T. K. Shkineva, G. P. Popova, S. A. Shevelev, “The specific reactivity of 3,4,5-trinitro-1H-pyrazole”, Mendeleev Commun., 20:5 (2010), 253–254
Linking options:
  • https://www.mathnet.ru/eng/mendc3055
  • https://www.mathnet.ru/eng/mendc/v20/i5/p253
  • This publication is cited in the following 49 articles:
    1. Mingya Wang, Hongxia Pan, Yongzheng Liu, Junli Shi, Fanfan Shen, Duanlin Cao, Linxiu Zhao, “Solubility Measurement, Correlation, and Hansen Solubility Parameter of 1,3-Dinitropyrazole in Twelve Solvents”, J Solution Chem, 2025  crossref
    2. Valery P. Sinditskii, Sergey P. Smirnov, Anastasia D. Smirnova, Nikolay V. Yudin, Kyaw O Ye, Trung H. Hoang, Igor L. Dalinger, “Trinitropyrazole derivatives: the features of thermal decomposition, combustion behaviors and mechanism”, FirePhysChem, 2025  crossref
    3. Ximei Yang, Chengming Bian, Fubing Yang, Cong Chen, Jianlong Wang, Zhinan Ma, Xia Li, Yueding Wu, Hongzhen Duan, “Amination of nitro-substituted fused triazole: A facile refinement for enhanced comprehensive performance”, Journal of Molecular Structure, 1313 (2024), 138739  crossref
    4. Yun-Hui Wu, Hua-Bei You, Wei-Kai Cui, Zhi-Qian Cao, Xiao Dong, Zi-Hui Meng, Ming Huang, “Monomeric and self-assembled crystal phases of TNBT”, Rare Met., 43:10 (2024), 5442  crossref
    5. Elena Reinhardt, Simon Thamm, Jörg Stierstorfer, Thomas M. Klapötke, “Alkyl‐Bridged Nitropyrazoles – Adjustment of Performance and Sensitivity Parameters”, Eur J Org Chem, 26:23 (2023)  crossref
    6. Yunlu Li, Mei Xue, Bangjin Sun, Zhenlong Tu, Xinzhong Wang, “Regulating the melting point by non-covalent interaction toward a promising insensitive melt-castable energetic material: 1,2-Difluoro-4,5-dinitrobenzene”, Chinese Journal of Structural Chemistry, 42:4 (2023), 100002  crossref
    7. Nikita V. Muravyev, Konstantin A. Monogarov, Igor L. Dalinger, Nobuyoshi Koga, Alla N. Pivkina, “Apparent autocatalysis due to liquefaction: thermal decomposition of ammonium 3,4,5-trinitropyrazolate”, Phys. Chem. Chem. Phys., 23:20 (2021), 11797  crossref
    8. Nikita V. Muravyev, Dmitry B. Meerov, Konstantin A. Monogarov, Igor N. Melnikov, Ekaterina K. Kosareva, Leonid L. Fershtat, Aleksei B. Sheremetev, Igor L. Dalinger, Igor V. Fomenkov, Alla N. Pivkina, “Sensitivity of energetic materials: Evidence of thermodynamic factor on a large array of CHNOFCl compounds”, Chemical Engineering Journal, 421 (2021), 129804  crossref
    9. G. M. Nazin, V. V. Dubikhin, I. L. Dalinger, A. I. Kazakov, A. V. Nabatova, “Influence of the Solvent's Polarity on the Rate of Thermal Decomposition of Nitropyrazoles”, Russ. J. Phys. Chem. B, 15:1 (2021), 74  crossref
    10. Tong-wei Zhang, Hao-qi Guo, Yong-xiang Li, Yong-zheng Liu, “Measurement and correlation of the solubility of 1-methyl-3,4,5-trinitropyrazole in twelve pure solvents at temperatures from 283.15 K to 323.15 K”, Journal of Molecular Liquids, 316 (2020), 113895  crossref
    11. Shijie Zhang, Zhenguo Gao, Di Lan, Qian Jia, Ning Liu, Jiaoqiang Zhang, Kaichang Kou, “Recent Advances in Synthesis and Properties of Nitrated-Pyrazoles Based Energetic Compounds”, Molecules, 25:15 (2020), 3475  crossref
    12. S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, “Nitro compounds as the core structures of promising energetic materials and versatile reagents for organic synthesis”, Russian Chem. Reviews, 89:1 (2020), 1–54  mathnet  mathnet  crossref  isi  scopus
    13. Laetitia Guyot, Florian Simon, Jessica Garcia, Floriane Vanhalle, Gaelle Vilchez, Claire Bardel, Brigitte Manship, Alain Puisieux, Christelle Machon, Guy Jacob, Jérôme Guitton, Léa Payen, “Structure-activity relationship study: Mechanism of cyto-genotoxicity of Nitropyrazole-derived high energy density materials family”, Toxicology and Applied Pharmacology, 381 (2019), 114712  crossref
    14. I. N. Zyuzin, A. I. Kazakov, D. B. Lempert, I. A. Vatsadze, L. S. Kurochkina, A. V. Nabatova, “Thermochemical and energy characteristics of alcoxy-NNO-azoxy derivatives of pyrazoles and nitropyrazoles”, Combustion, Explosion and Shock Waves, 55:3 (2019), 327–334  mathnet  mathnet  crossref  crossref
    15. Tatyana K. Shkineva, Alexandr V. Kormanov, Valeriya N. Boldinova, Irina A. Vatsadze, Igor L. Dalinger, “Synthesis of 4,4'-dinitro-1H,1'H-[3,3'-bipyrazole]-5,5'-diamine”, Chem Heterocycl Comp, 54:7 (2018), 703  crossref
    16. Igor N. Zyuzin, Kirill Yu. Suponitsky, Igor L. Dalinger, “N-[2,2-Bis(methoxy-NNO-azoxy)ethyl]pyrazoles”, Chem Heterocycl Comp, 53:6-7 (2017), 702  crossref
    17. V.P. Sinditskii, S.P. Smirnov, V.Yu. Egorshev, A.N. Chernyi, T.K. Shkineva, N.V. Palysaeva, K.Yu. Suponitsky, I.L. Dalinger, “Thermal decomposition peculiarities and combustion behavior of nitropyrazoles”, Thermochimica Acta, 651 (2017), 83  crossref
    18. T. S. Kon'kova, E. A. Miroshnichenko, A. B. Vorob'ev, Yu. N. Matyushin, T. K. Shkineva, I. L. Dalinger, “Enthalpies of formation of nitrodiazoles”, Russ Chem Bull, 65:11 (2016), 2612  crossref
    19. Thomas M. Klapötke, Tomasz G. Witkowski, “Covalent and Ionic Insensitive High‐Explosives”, Propellants Explo Pyrotec, 41:3 (2016), 470  crossref
    20. V. V. Dubikhin, G. M. Nazin, V. G. Prokudin, Z. G. Aliev, I. L. Dalinger, S. A. Shevelev, “Thermal stability of 3,4,5-trinitropyrazole and its ammonium salt”, Russ. J. Phys. Chem. B, 9:2 (2015), 211  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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