Compounds based on 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan as insensitive energetic materials

Yu, Qingbo; Cheng, Guangbin; Ju, Xue‐Hai; Lu, Chunmei; Lin, Qiuhan; Yang, Hongwei

doi:10.1039/c6nj03333d

Cited by 27 publications

(9 citation statements)

References 39 publications

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“…3,4-Bis(nitramino)furazan (Scheme 1A), a typical example that has a high density of 1.899 g cm −3 , is impossible to be applied due to its high sensitivities (IS < 1 J and FS < 5 J) ( Figure 1A) (Tang et al, 2015). Although the replacement of a nitramino group with a 5-methyl-1,2,4-oxadiazole (Scheme 1B) moiety can evidently improve the insensitivity (IS = 37.8 J and FS > 360 N), the energetic level of 3-nitramino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan methyl(-CH 3 ) becomes much lower (ρ = 1.65 cm −1 and v D = 7,810 m s −1 ) due to the existence of non-energetic methyl group (Yu et al, 2017) (Figure 1B).…”

Section: Introductionmentioning

confidence: 99%

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

Xue¹,

Bi²,

Zhang³

et al. 2020

Front. Chem.

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Design and synthesis of new compounds with both high detonation performances and good safety properties have always been a formidable task in the field of energetic materials. By introducing -ONO 2 and -NHNO 2 moieties into 1,2,4-oxadiazole-and 1,2,5-oxadiazole-based backbones, a new family of energetic materials, including ammonium 3-nitramino-4-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)-furazan (4), 3,3 ′ -bis[5-nitroxymethyl-1,2,4-oxadiazol-3-yl]-4,4 ′azofuroxan (6), [3-(4-nitroamino-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl]-methylene nitrate (8), and its energetic ionic salts (10-12), were synthesized and fully characterized. The energetic and physical properties of the materials were investigated through theoretical calculations and experimental determination. The results show that the oxadiazole-based compounds exhibit high enthalpy of formations, good detonation performances, and extraordinary insensitivities. In particular, the hydrazinium salt (11) shows the best energetic properties (11: d =1.821 g cm −3 ; P = 35.1 GPa, v D = 8,822 m s −1 , IS = 40 J, FS > 360 N). The ESP and Hirshfeld surface analysis indicated that a large number of hydrogen bonds as well as π-π stacking interactions within molecules might be the key reason for their low sensitivities and high energy-density levels.

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Section: Introductionmentioning

confidence: 99%

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

Xue¹,

Bi²,

Zhang³

et al. 2020

Front. Chem.

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“…Amazingly, the plane of gem ‐dinitromethyl groups in 2 and 5 show an obvious conformation with approximately perpendicular to triazine ring based on the torsion angles. However, the torsion angle in salt 7 is closed to 0°, and this twist most possibility can be ascribed to the more hydrogen‐bonding interactions between cation and anion , …”

Section: Resultsmentioning

confidence: 99%

Nitrogen‐rich Salts based on 3‐Dinitromethyl‐[1,2,4]triazine: Synthesis, Characterization, and Performance

Dong

Yang

et al. 2019

Zeitschrift anorg allge chemie

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1,1-Diamino-2,2-dinitroethylene (FOX-7), one of the most well-known energetic materials, has attracted broad attention around the world. To extend the chemistry of FOX-7, we present here a series of energetic salts based on 3-dinitromethyl-[1,2,4]triazine, which is prepared from FOX-7. All these salts were fully characterized using 1 H NMR, 13 C NMR, IR, and elemental analysis. In addition, the potassium salt (2), ammonium salt (5), and guanidinium salt (7) were further confirmed by single-crystal X-ray diffraction. Extensive hydrogen * Dr. Z. Ye E-Mail: yezw@njust.edu.cn [a] School of Chemical Engineering

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“…Compound 75 a was further introduced in Mannich condensation with trinitroethanol (TNE) followed by nitration of formed Mannich base 85 resulting in nitramine 86 . In addition, to find a balance between explosive properties and safety the initial compound 75 a was transformed into nitramine 87 , which served as a matrix for the preparation of salts 88 a‐i by simple acid‐base reaction with different high‐nitrogen amines (Scheme ) …”

Section: Assembly Of 125‐oxadiazole Ring With 124‐ and 134‐oxadmentioning

confidence: 99%

“…Energetic salts 88 a – i exhibit good thermal stabilities (203–255 °C) and low sensitivities (IS>40 J; FS>360 N). The majority of the synthesized salts have shown higher detonation properties ( D =8024–8545 m s −1 , P =25.0–30.2 GPa) than those of nitramine 87 ( D =7810 m s −1 , P =24.1 GPa) and TNT ( D =7304 m s −1 , P =21.3 GPa) . These results suggest that energetic (1,2,4‐oxadiazolyl)furazan derivatives might be of interest for applications as insensitive energetic materials.…”

Section: Assembly Of 125‐oxadiazole Ring With 124‐ and 134‐oxadmentioning

confidence: 99%

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

2019

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This Review covers the synthesis and performance of the most promising 1,2,5-oxadiazole-based high-energy density materials (HEDMs). These materials comprise a 1,2,5-oxadiazole subunit as a key structural motif linked to various acyclic explosophoric groups or to nitrogen-rich and nitrogen-oxygen azoles: 1,2,4triazole, tetrazole, 1,2,4-and 1,3,4-oxadiazoles. Energetic alliances of two and more 1,2,5-oxadiazole rings linked directly or through heteroatom spacers are also presented. Particular attention is devoted to the installation of different explosophores: nitro, nitramino, azo, azoxy, dinitromethyl, trinitroethyl moieties and their combination. Promising environmentally benign energetic materials with high detonation velocity and pressure, and outstanding insensitivity are summarized. Overall, the presented materials may be considered as next-generation high-performance energetic materials that are superior to commonly used traditional explosives (TNT, PETN, RDX, HMX).

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Compounds based on 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan as insensitive energetic materials

Abstract: Insensitivity: Derivatives based on 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan were synthesized and characterized. Most of these compounds are thermally stable and insensitive which make them competitive replacement as insensitive energetic materials.

Cited by 27 publications

References 39 publications

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

Nitrogen‐rich Salts based on 3‐Dinitromethyl‐[1,2,4]triazine: Synthesis, Characterization, and Performance

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

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