A promising cation of 4-aminofurazan-3-carboxylic acid amidrazone in desensitizing energetic materials

Zhang, Jiaheng; Wang, Zhenyuan; Hsieh, Yun‐Hao; Wang, Binshen; Huang, Haifeng; Yang, Jeong-Mo

doi:10.1039/c9ra09555a

“…Energetic salts composed of anions and cations exhibit the characteristics of ionic compounds. These include a low vapor pressure, excellent thermal stability, a high density, and minimal environmental impacts, therefore representing extensive application potential [12]. The studies available in the literature have revealed that the incorporation of methyl groups into the molecular structure of these salts can prove effective in reducing sensitivity and enhancing safety, as well as elevating the decomposition temperature of energetic materials [13,14].…”

Section: Introductionmentioning

confidence: 99%

Polyvalent Ionic Energetic Salts Based on 4-Amino-3-hydrazino-5-methyl-1,2,4-triazole

Lin,

Zhang,

Zhang

et al. 2023

IJMS

0

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The synthesis of the new energetic material 4-amino-3-hydrazino-5-methyl-1,2,4-triazole, which shows excellent performance and reliable safety, has drawn attention recently. To fully characterize this material, a comprehensive analysis was performed using various techniques, including differential scanning calorimetry (DSC), infrared spectroscopy (IR), elemental analysis, and 1H and 13C NMR spectroscopy. Additionally, three compounds, 3, 5 and 9, were further characterized using single X-ray diffraction. The X-ray data suggested that extensive hydrogen bonds affect molecular structure by means of intermolecular interactions. In order to evaluate the explosive properties of these synthesized compounds, detonation pressures and velocities were calculated using EXPLO5 (V6.01). These calculations were carried out utilizing experimental data, including density and heat of formation. Among the explosives tested, compounds 7 and 8 exhibited zero oxygen balance and demonstrated exceptional detonation properties. Compound 7 achieved the highest recorded detonation pressure, at 34.2 GPa, while compound 8 displayed the highest detonation velocity, at 8887 m s−1.

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Simple and Versatile Nitrooxylation: Noncyclic Hypervalent Iodine Nitrooxylating Reagent

Cheng

¹

,

Yin

²

,

Jiang

³

et al. 2023

Angewandte Chemie

0

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Organic nitrates are broadly applied as pharmaceuticals (acting as efficient nitric oxide donor), energetic materials, building blocks in organic synthesis, etc. However, practical and direct methods to access organic nitrates efficiently are still rare, mainly due to the lack of powerful nitrooxylating reagents. Herein, we report bench-stable and highly reactive noncyclic hypervalent iodine nitrooxylating reagents, oxybis(aryl-λ 3iodanediyl) dinitrates (OAIDNs, 2), which are prepared just by using aryliodine diacetate and HNO 3 . The reagents are used to achieve a mild and operationally simple protocol to access diverse organic nitrates. By employing of 2, zinc-catalyzed regioselective nitrooxylation of cyclopropyl silyl ethers is realized efficiently to access the corresponding β-nitrooxy ketones with high functional-group tolerance. Moreover, a series of direct and catalyst-free nitrooxylations of enolizable CÀ H bonds are carried out smoothly to afford the desired organic nitrates within minutes by just mixing the substrates with 2 in dichloromethane.

show abstract

Simple and Versatile Nitrooxylation: Noncyclic Hypervalent Iodine Nitrooxylating Reagent

Cheng

¹

,

Yin

²

,

Jiang

³

et al. 2023

View full text Add to dashboard Cite

Organic nitrates are broadly applied as pharmaceuticals (acting as efficient nitric oxide donor), energetic materials, building blocks in organic synthesis, etc. However, practical and direct methods to access organic nitrates efficiently are still rare, mainly due to the lack of powerful nitrooxylating reagents. Herein, we report bench-stable and highly reactive noncyclic hypervalent iodine nitrooxylating reagents, oxybis(aryl-λ 3iodanediyl) dinitrates (OAIDNs, 2), which are prepared just by using aryliodine diacetate and HNO 3 . The reagents are used to achieve a mild and operationally simple protocol to access diverse organic nitrates. By employing of 2, zinc-catalyzed regioselective nitrooxylation of cyclopropyl silyl ethers is realized efficiently to access the corresponding β-nitrooxy ketones with high functional-group tolerance. Moreover, a series of direct and catalyst-free nitrooxylations of enolizable CÀ H bonds are carried out smoothly to afford the desired organic nitrates within minutes by just mixing the substrates with 2 in dichloromethane.

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A promising cation of 4-aminofurazan-3-carboxylic acid amidrazone in desensitizing energetic materials

Abstract: 4-Aminofurazan-3-carboxylic acid amidrazone was used to obtain four derivatives confirmed by X-ray diffraction. The derivatives are insensitive to impact and friction, while the velocities of detonation are superior to that of 1,3,5-triamino-2,4,6-trinitrobenzene.

Cited by 5 publications

References 38 publications

Polyvalent Ionic Energetic Salts Based on 4-Amino-3-hydrazino-5-methyl-1,2,4-triazole

Polyvalent Ionic Energetic Salts Based on 4-Amino-3-hydrazino-5-methyl-1,2,4-triazole

Simple and Versatile Nitrooxylation: Noncyclic Hypervalent Iodine Nitrooxylating Reagent

Simple and Versatile Nitrooxylation: Noncyclic Hypervalent Iodine Nitrooxylating Reagent

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