5-substituted 3-nitro-1-trinitromethyl-1,2,4-triazoles

Kofman, T. P.; Kartseva, G. Yu.; Glazkova, E. Yu.

doi:10.1134/s107042800806016x

Cited by 22 publications

(14 citation statements)

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“…In order to obtain high-performance green primary explosives with good characteristics (higher detonation performance, good oxygen balance, and better density), various energetic groups are introduced, such as 1,2,4-triazole (3-amino-5-nitro-1,2,4-triazole (ANTA)) backbone. [53] Subsequently, a series of novel HEDMs were prepared by the reaction of N-(3-nitro-1-(trinitromethyl)-1H-1,2,4-triazol-5-yl)nitramide (consist of three energetic groups, i. e., trinitromethyl, nitramino, and nitro groups) with different bases. When reactant was treated with different bases such as ammonia, hydroxylamine monohydrate, hydrazine monohydrate, 4-amine-1,2,4-triazol, 5-amine-tetrazol, and 3,5-diamine-1,2,4-triazole, energetic salts 16-22 were obtained (Scheme 2(g)) in high yield (78-84 %).…”

Section: Nomentioning

confidence: 99%

“…In order to obtain high‐performance green primary explosives with good characteristics (higher detonation performance, good oxygen balance, and better density), various energetic groups are introduced, such as 1,2,4‐triazole (3‐amino‐5‐nitro‐1,2,4‐triazole (ANTA)) backbone [53] . Subsequently, a series of novel HEDMs were prepared by the reaction of N‐(3‐nitro‐1‐(trinitromethyl)‐1H‐1,2,4‐triazol‐5‐yl)nitramide (consist of three energetic groups, i. e., trinitromethyl, nitramino, and nitro groups) with different bases.…”

Section: Metal‐free Primary Explosivesmentioning

confidence: 99%

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Synthesis and Energetic Properties of Trending Metal‐Free Potential Green Primary Explosives: A Review

et al. 2022

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The requirements for the chemical to act as a primary explosive, its importance, and the hazards associated with heavy‐metal‐based primary explosives are all well‐stated in this review. In addition, it outlined the limitations of the heavy‐metal‐free primary explosives already in use. This analysis underlines the importance of green primary explosives with updated information. It summarizes the possible candidates of metal‐free new generation green primary explosives, including their preparation routes, energetic properties, applications, and comparisons to traditional primary explosives. Furthermore, this analysis also aims to discuss the necessity for metal‐free primary explosives as well as the significant problem of replacing traditional primary explosives.

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Section: Nomentioning

confidence: 99%

Section: Metal‐free Primary Explosivesmentioning

confidence: 99%

Synthesis and Energetic Properties of Trending Metal‐Free Potential Green Primary Explosives: A Review

et al. 2022

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“…N -Propanonyl or N -butanonyl azoles can be readily converted to N -trinitromethyl functionalized energetic compounds in a mixture of sulfuric acid and nitric acid (Scheme ). Highly selective syntheses of N -dinitromethyl azoles were achieved by using water as the additive . A series of N -trinitromethyl pyrazoles was synthesized among which the polynitro compound 1-49 exhibited a positive oxygen balance (Ω CO 2 = +7.8%) and a high density of 1.94 g cm –3 .…”

Section: Synthesis Of High-energy Density Materials Involving An N–c ...mentioning

confidence: 99%

“…In the presence of trifluoroacetic anhydride and 50% hydrogen peroxide, a series of tetrazine-1-N-oxides and tetrazine-2,4-di-N-oxides was prepared (Scheme 15). 52,53 In a single case, the N-oxidation process was accompanied by the transformation of a C-amino group into a C-nitro group (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21), that is, N-oxidation of 6-azido-1,2,4,5-tetrazin-3-amine gave rise to a fused tetrazine−tetrazole structure with an N→O functionality, with a high density of 1.874 g cm −3 and relatively low sensitivities (IS, 10 J; FS, 80 N).…”

Section: ■ Introductionmentioning

confidence: 99%

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

2015

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Nitrogen-rich heterocycles represent a unique class of energetic frameworks featuring high heats of formation and high nitrogen content, which have generated considerable research interest in the field of high energy density materials (HEDMs). Although traditional C-functionalization methodology of aromatic hydrocarbons has been fully established, studies on N-functionalization strategies of nitrogen-containing heterocycles still have great potential to be exploited by virtue of forming diverse N-X bonds (X = C, N, O, B, halogen, etc.), which are capable of regulating energy performance and the stability of the resulting energetic compounds. In this sense, versatile N-functionalization of N-heterocyclic frameworks offers a flexible strategy to meet the requirements of developing new-generation HEDMs. In this Account, the role of strategic N-functionalization in designing new energetic frameworks, including the formation of N-C, N-N, N-O, N-B and N-halogen bonds, is emphasized. In the family of N-functionalized HEDMs, energetic derivatives, by virtue of forming N-C bonds, are the most widely used type due to the good nucleophilic capacity of most heterocyclic backbones. Although introduction of carbon tends to decrease energetic performance, significant improvement in material sensitivity makes this strategy attractive for safety concerns. More importantly, most "explosophores" can be readily introduced into the N-C linkage, thus providing a promising route to various HEDMs. Formation of additional N-N bonds typically gives rise to higher heats of formation, implying the potential enhancement in detonation performance. In many cases, the increased hydrogen bonding interactions within N-N functionalized heterocycles also improve thermal stability accordingly. Introduction of a single N,N'-azo bridge into several azole moieties leads to an extended nitrogen chain, demonstrating a new strategy for designing high-nitrogen compounds. The strategy of N-O functionalization has become an increasingly efficient tool for exploring new HEDMs with both high energy and low sensitivity. As a highly dense building block, introduction of oxygen not only improves density significantly but also gives rise to a better oxygen balance. Furthermore, the N-O functionalized strategy is highly suitable for a broad variety of N-heterocycles including five-membered azoles and six-membered azines. Newly explored N-halogen and N-B functionalization strategies have endowed the resulting HEDMs with some new energetic characteristics. Typical examples include the N-halogenated fused triazole and FOX-7 as potential hypergolic oxidizers with very short ignition delay times. In addition, some exploratory studies of N-B functionalized heterocycles have expanded energetic applications as hypergolic ionic liquids, green pyrotechnic colorants, and high-oxygen carriers. Overall, flexible N-functionalization methodologies involving different N-X bond formation have not only provided an efficient approach to diverse energetic ingredients but also expanded...

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“…The synthetic protocol is given in Scheme 1. The destructive nitration step is basedo nt he original worko f Kofman et al whou sed this approacht op repare the N-trinitrometyl-1,2,4-triazoles from (3-R-1,2,4-triazol-1-yl)propan-2-ones [13,14].…”

Section: Introductionmentioning

confidence: 99%

Novel Melt‐Castable Energetic Pyrazole: A Pyrazolyl‐Furazan Framework Bearing Five Nitro Groups

Далингер

Suponitsky

Пивкина

et al. 2016

Propellants Explo Pyrotec

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Continuing advances in energetic pyrazole construction foster further its rational use. This work establishes an approach for the first synthesis of nitropyrazole that bear both furazan and trinitromethyl moieties. The approach to the installation of the C(NO2)3 group exploits the destructive nitration of N‐acetonyl group. The target 3‐(3,4‐dinitro‐1‐(trinitromethyl)‐1H‐pyrazol‐5‐yl)‐4‐methylfurazan (6) has promising explosive properties.

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5-substituted 3-nitro-1-trinitromethyl-1,2,4-triazoles

Cited by 22 publications

References 1 publication

Synthesis and Energetic Properties of Trending Metal‐Free Potential Green Primary Explosives: A Review

Synthesis and Energetic Properties of Trending Metal‐Free Potential Green Primary Explosives: A Review

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

Novel Melt‐Castable Energetic Pyrazole: A Pyrazolyl‐Furazan Framework Bearing Five Nitro Groups

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