Synthesis, structure and properties of neutral energetic materials based on N-functionalization of 3,6-dinitropyrazolo[4,3-c]pyrazole

Li, Yanan; Shu, Yuanjie; Wang, Bozhou; Zhang, Shengyong; Zhai, Lianjie

doi:10.1039/c6ra19556c

Cited by 27 publications

(15 citation statements)

References 55 publications

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“…There has been a considerable amount of research in the field of thermally stable explosives during the last decade and as a result, a number of explosives have been reported in the literature [31–51] . A brief description of their synthetic aspects, structural analysis, thermal and explosive properties are given in this section & Table 2.…”

Section: Resultsmentioning

confidence: 99%

“…(iv) Zhou, Zhang and Associates [38] have reported a novel explosive featuring a 3‐dimensional (3D) metal‐organic framework (MOF) designated as KCPT [Potassium 4‐(5‐amino‐3‐nitro‐1 H ‐1,2,4‐triazol‐1‐yl)‐3,5‐dinitropyrazole] by a simple one step regioselective coupling of 5‐amino‐3‐nitro‐1 H ‐1,2,4‐triazole (ANTA) [39–41] with trinitropyrazole (TNP) [42–44] as per Scheme 6 shown below:…”

Section: Resultsmentioning

confidence: 99%

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Some Novel High Energy Materials for Improved Performance**

Agrawal

Dodke²

2021

Zeitschrift anorg allge chemie

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High Energy Materials (HEMs) is a generic/umbrella term which is used for explosives, propellants & pyrotechnics and form an integral part of almost all weapon systems. A large number of HEMs have been reported in the literature in last few decades. This review paper discusses these HEMs in the light of a new classification of explosives proposed by Agrawal: Thermally stable or Heat‐resistant explosives, High performance (high density & high velocity of detonation) explosives, Melt‐Castable explosives, Insensitive high explosives (IHEs), Energetic binders & plasticizers and Novel energetic materials synthesized with the use of dinitrogen pentoxide (N2O5) technology. This review also critically examines these HEMs from the angles of scalability, processability, safety, reliability and performance in order to ascertain their potential for applications. In the end, problems associated with the use of currently available energetic materials & their likely solutions and areas for further research are also highlighted.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Some Novel High Energy Materials for Improved Performance**

Agrawal

Dodke²

2021

Zeitschrift anorg allge chemie

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“…Compounds 126a, 126b, 126c and 126g showed good possibilities for application in bipropellants owing to the high values of (N + O) content and specific impulse. Li and co-author [142] synthesized another four kinds of neutral explosives based on N-functionalization of DNPP shown in Scheme B of Figure 40. Comparing with LLM-119, compound 127 showed slightly lower energetic and physical properties due to the only one -NH 2 .…”

Section: Nitrated Pyrazolo[43-c]pyrazoles and Their Derivativesmentioning

confidence: 99%

“…Physical and detonation properties of energetic compounds LLM-119 and from reference[141], the data of compounds 127-130 are from reference[142].…”

mentioning

confidence: 99%

Recent Advances in Synthesis and Properties of Nitrated-Pyrazoles Based Energetic Compounds

et al. 2020

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Nitrated-pyrazole-based energetic compounds have attracted wide publicity in the field of energetic materials (EMs) due to their high heat of formation, high density, tailored thermal stability, and detonation performance. Many nitrated-pyrazole-based energetic compounds have been developed to meet the increasing demands of high power, low sensitivity, and eco-friendly environment, and they have good applications in explosives, propellants, and pyrotechnics. Continuous and growing efforts have been committed to promote the rapid development of nitrated-pyrazole-based EMs in the last decade, especially through large amounts of Chinese research. Some of the ultimate aims of nitrated-pyrazole-based materials are to develop potential candidates of castable explosives, explore novel insensitive high energy materials, search for low cost synthesis strategies, high efficiency, and green environmental protection, and further widen the applications of EMs. This review article aims to present the recent processes in the synthesis and physical and explosive performances of the nitrated-pyrazole-based Ems, including monopyrazoles with nitro, bispyrazoles with nitro, nitropyrazolo[4,3-c]pyrazoles, and their derivatives, and to comb the development trend of these compounds. This review intends to prompt fresh concepts for designing prominent high-performance nitropyrazole-based EMs.

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“…Nitropyrazoles are significant for the design and synthesis of energetic materials [ 8 , 9 ]. During the past few decades, our research interest was mainly focused on the structural diversity of fused-heterocyclic frameworks in energetic materials, among which, the pyrazolo [4,3-c]pyrazole structure was a successfully applied framework in the construction of 1 H ,4 H -3,6-dinitropyrazolo [4,3- c ]pyrazole (DNPP), as well as its insensitive derivative [ 10 , 11 , 12 , 13 ], 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole (LLM-119) [ 14 ], which contains both amino and nitro groups. 1 H ,4 H -3-Amino-6-nitropyrazolo[4,3- c ]pyrazole (ANPP) is another pyrazolo[4,3-c]pyrazole framework-based insensitive energetic material that is ideal as the key intermediate for subsequent transformations in the design and synthesis of multiple kinds of pyrazole-based energetic materials [ 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Energetic 7-Nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one Based on a Novel Hofmann-Type Rearrangement

Bi¹,

Luo²,

Zhang

et al. 2021

Molecules

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Rearrangement reactions are efficient strategies in organic synthesis and contribute enormously to the development of energetic materials. Here, we report on the preparation of a fused energetic structure of 7-nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one (NPTO) based on a novel Hofmann-type rearrangement. The 1,2,3-triazine unit was introduced into the fused bicyclic skeleton from a pyrazole unit for the first time. The new compound of NPTO was fully characterized using multinuclear NMR and IR spectroscopy, elemental analysis as well as X-ray diffraction studies. The thermal behaviors and detonation properties of NPTO were investigated through a differential scanning calorimetry (DSC-TG) approach and EXPLO5 program-based calculations, respectively. The calculation results showed similar detonation performances between NPTO and the energetic materials of DNPP and ANPP, indicating that NPTO has a good application perspective in insensitive explosives and propellants.

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Synthesis, structure and properties of neutral energetic materials based on N-functionalization of 3,6-dinitropyrazolo[4,3-c]pyrazole

Abstract: Various neutral energetic derivatives based onN-functionalization of DNPP were synthesized, which can be used as new high energy-density materials.

Cited by 27 publications

References 55 publications

Some Novel High Energy Materials for Improved Performance**

Some Novel High Energy Materials for Improved Performance**

Recent Advances in Synthesis and Properties of Nitrated-Pyrazoles Based Energetic Compounds

Synthesis of Energetic 7-Nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one Based on a Novel Hofmann-Type Rearrangement

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