A Simple and Environmentally Benign Nitration of Pyrazoles by Impregnated Bismuth Nitrate

Ravi, P.; Gore, G. M.; Tewari, Surya P.; Sikder, A. K.

doi:10.1002/jhet.1093

Cited by 9 publications

(4 citation statements)

References 26 publications

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“…After stirring for 12 h, and evaporation of trifluoroacetic anhydride and nitric acid, the 3-MNP could be obtained (Figure 1, Scheme C). In 2013, Ravi et al [46] proposed that 1-methylpyrazole could reacted with silicon oxide-bismuth nitrate or silicon dioxide-sulfuric acid-bismuth nitrate in tetrahydrofuran (THF) to produce 3-MNP ( Figure 1, Scheme D), this facile route is a synthetic method of low toxicity, high efficiency, and green environmental protection. In addition, metal salts of 3-NP expand its derivatives.…”

Section: Mononitropyrazoles and Their Derivativesmentioning

confidence: 99%

“…The N-trinitroethylamination of dinitropyrazole was firstly proposed by Shreeve team [57]. They obtained several N-amino-dinitropyrazoles firstly, then these compounds underwent Mannich reactions with trinitroethanol to acquire the corresponding derivatives (46)(47)(48)(49)(50) (Figure 18, Scheme A). It was noteworthy that 1-amino-3,5-dinitropyrazole and 1-amino-3,4-dinitro-5-cyanopyrazole failed to get the corresponding compounds due to the electron-withdrawing effect of substituent groups bonded to dinitropyrazole ring.…”

Section: % 73%mentioning

confidence: 99%

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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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Section: Mononitropyrazoles and Their Derivativesmentioning

confidence: 99%

Section: % 73%mentioning

confidence: 99%

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

et al. 2020

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“…In order to better understand the effect of positional isomerism on the energetic melt-castable isomers. Herein, we selected effective precursors (4-chloro-1-methyl-3,5-dinitropyrazole (ClMDNP) and 1-methyl-3,4,5-trinitropyrazole (MTNP)) according to the difference in the reaction sites − and obtained two positional isomers 4-methylnitramino-1-methyl-3,5-dinitropyrazole (namely, 4-MMDNP) and 5-methylnitramino-1-methyl-3,4-dinitropyrazole (namely, 5-MMDNP) through a facile two-step reaction. They showed drastically different physicochemical properties, including melting point (Δ T m = 47.2 °C), thermostability (Δ T d = 27.3 °C), detonation performance (Δ D v = 120 m s –1 ), etc.…”

Section: Introductionmentioning

confidence: 99%

Impact of Positional Isomerism on Melting Point and Stability in New Energetic Melt-Castable Materials

et al. 2023

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For an energetic material with a definite composition, the substituent position is the most crucial factor to influence its physicochemical properties. Thus, it is becoming increasingly important to understand the impact of positional isomerism on multidimensional properties differences. Herein, we reported two new potential energetic melt-castable molecules, a pair of positional isomers (4-MMDNP and 5-MMDNP). These two explosives exhibit obviously different properties, including densities (Δρ = 0.03 g cm −3 ), melting point (ΔT m = 47.2 °C), decomposition temperature (ΔT d = 27.3 °C), stability (IS = 20 J, FS = 160 N vs IS = 10 J, FS = 40 N), etc., even though they share similar compositions and structures. Simultaneously, by analyzing crystal packing, intermolecular interactions, and monomolecular parameters, we were able to uncover the roots of property differences. Altogether, our results provide comprehensive molecular and crystal level insight into the effect of positional isomerism, which may be useful for new molecular design.

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“…Dalinger 等[53] 采用硝酸/硫酸作为硝化试剂硝化 3,5-二硝基吡唑, 以 87%的收率得到 TNP. Ravi 等[54][55] 用金属硝酸盐为硝化试剂对 3,5-二硝基吡唑进行硝化, TNP 的制备收率在 90%以上 . 赵秀秀等[56] 采用过硫酸氢钾 (Oxone)氧化 LLM-116, 以 85%的收率得到 TNP.…”

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Progress in the Synthesis of Energetic Salts Based on Pyrazole

Li¹,

Huang²,

Yang³

et al. 2021

Chinese Journal of Organic Chemistry

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The pyrazole ring has three modifiable carbon sites and one modifiable NH site. Based on the pyrazole ring, a variety of pyrazole energetic compounds can be designed by the introduction of nitro, nitramino, amino and hydroxyl group and the formation of fused rings. At the same time, compared with conventional energetic compounds such as 2,4,6-trinitrobenzene (TNT), hexahydro-1,3,5-trinitro-triazine (RDX) and 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX), energetic pyrazoles have the advantages of high nitrogen content, high enthalpy of formation and low sensitivities. In recent years, a large number of energetic salts based on pyrazole have been designed and synthesized around the world, including monocyclic energetic salts, bicyclic energetic salts and fused energetic salts based on pyrazole. Many of them exhibit the characteristics of high energy and low sensitivity. The synthesis and properties of recently reported energetic salts based on pyrazole are reviewed, and their applications in the field of energetic materials are prospected.

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A Simple and Environmentally Benign Nitration of Pyrazoles by Impregnated Bismuth Nitrate

Cited by 9 publications

References 26 publications

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

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

Impact of Positional Isomerism on Melting Point and Stability in New Energetic Melt-Castable Materials

Progress in the Synthesis of Energetic Salts Based on Pyrazole

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