Energetic 1,2,5‐Oxadiazolo‐Pyridazine and its N‐Oxide

Tang, Yongxing; He, Chunlin; Imler, Gregory H.; Parrish, Damon A.; Shreeve, Jean’ne M.

doi:10.1002/chem.201703930

Cited by 31 publications

(11 citation statements)

References 47 publications

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“…13 General Procedure for the Synthesis of Energetic Salts (5−8). The preparation of these energetic salts was conducted according to the reported ref 35. Compound 4 (0.48 g, 2.0 mmol) was suspended in water (15 mL), and 1 equiv of ammonia or 50% hydroxylamine, hydrazine monohydrate, or potassium hydroxide was added.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Efficient Synthesis of a Superior Heat-Resistant Energetic Material Based on Fused Pyrazolotriazine Ring

Huang

et al. 2021

Crystal Growth & Design

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Fused-ring energetic materials are considered to be promising energetic materials. However, their practical applications are usually hindered due to the tedious synthetic routes. In this work, 4-amino-3,8-dinitropyrazolo[5,1-c][1,2,4]triazin-7-ol (4) was easily prepared within three straightforward steps starting from commercially available ethyl cyanoglyoxylate 2-oxime (1). Compound 4 is a promising heat-resistant explosive, with remarkable thermal stability (decomposition temperature 332 °C) and thermal sensitivity (burst point 380 °C at 5 s). In addition, it demonstrates high density (1.88 g cm–3), good detonation velocity (8538 m s–1), and low impact and friction sensitivities (IS > 40 J; FS > 360 N). Optimized conditions for the synthesis of 4 have also been investigated, and a scale of 10 g could be prepared over one-batch reaction using the modified synthetic path with a high overall yield (46%). The advanced performance and scalable production of 4 make it a bright prospect for industrial production.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Efficient Synthesis of a Superior Heat-Resistant Energetic Material Based on Fused Pyrazolotriazine Ring

Huang

et al. 2021

Crystal Growth & Design

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“…Given this background, a novel nitrogen-rich fused heterocyclic cation 1H-imidazo [4,5-d]pyridazine-2,4,7-triamine was synthesized by a one-step reaction from 4,5dicyano-2-aminoimidazole and hydrazine hydrate. 18 Then, by reacting with perchloric acid at room temperature, 1Himidazo [4,5-d]pyridazine-2,4,7-triamine perchlorate (α-4) was obtained and confirmed by X-ray single crystal diffraction. 1H-Imidazo [4,5-d]pyridazine-2,4,7-triamine perchlorate shows high density (1.93 g cm −3 ), good exothermic behavior (274 °C), and acceptable mechanical sensitivity (IS, 14 J; FS, 168 N).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Given this background, a novel nitrogen-rich fused heterocyclic cation 1 H -imidazo[4,5- d ]pyridazine-2,4,7-triamine was synthesized by a one-step reaction from 4,5-dicyano-2-aminoimidazole and hydrazine hydrate . Then, by reacting with perchloric acid at room temperature, 1 H -imidazo[4,5- d ]pyridazine-2,4,7-triamine perchlorate ( α-4 ) was obtained and confirmed by X-ray single crystal diffraction.…”

Section: Introductionmentioning

confidence: 99%

Energetic 1H-Imidazo[4,5-d]pyridazine-2,4,7-triamine: A Novel Nitrogen-rich Fused Heterocyclic Cation with High Density

Jia

Zhang

et al. 2020

Crystal Growth & Design

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Fused heterocyclic energetic cation was rarely reported despite the development of energetic cation has attracted increasing attention in recent years. In this work, a new 1H-imidazo[4,5-d]pyridazine-2,4,7-triamine was synthesized in a one-step reaction, which was used as a cation to prepare 1H-imidazo[4,5-d]pyridazine-2,4,7-triamine perchlorate. Interestingly, when the synthesis was accomplished in different conditions, two crystal forms of perchlorate α-4 and β-4 were obtained, which were further confirmed by X-ray single crystal diffraction, X-ray powder diffractograms, infrared and multinuclear NMR spectra. These salts showed high density (1.88–1.93 g cm–3 at 293(2) K), moderate detonation performance (D, 8128–8437 m s–1; P, 29.4–32.86 GPa) and good thermal stability (T d: 272–274 °C). Compared with those known energetic perchlorates, the density and sensitivity (IS, 14–20 J; FS, 144–168 J) of 4 were also significantly improved. Through theoretical calculations and experiment results, the explanations for the differences in physicochemical properties of these two crystal forms were illustrated. Density overlap indicator (DORI) analysis was also employed to perform the necessary visualization and quantification of covalent and noncovalent interactions. It is evident that ionic bonds, hydrogen bonds, and π–π interactions are responsible for the high density and excellent performance of 1H-imidazo[4,5-d]pyridazine-2,4,7-triamine perchlorate, indicating that as-synthesized new material is a very promising cation in the construction of low-sensitivity high-energy compounds.

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“…In addition, the nitro group is an excellent leaving group and can be easily substituted even by weak nucleophiles . However, recently reported literature shows that 1,2‐diazine (pyridazine) derivatives and their N ‐oxides can be synthesized and may be interesting new building blocks for the synthesis of new energetic materials . The idea of this work was to synthesize 3,5‐diamino‐4,6‐dinitropyridazine‐1‐oxide and 4,6‐diamino‐3,5‐dinitropyridazine‐1‐oxide (Figure ); two structural isomers to LLM‐105, which are based on the pyridazine scaffold.…”

Section: Introductionmentioning

confidence: 99%

Energetic Functionalization of the Pyridazine Scaffold: Synthesis and Characterization of 3,5‐Diamino‐4,6‐dinitropyridazine‐1‐Oxide

2018

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The synthesis of 3,5‐diamino‐4,6‐dinitropyridazine‐1‐oxide (8) is reported. It is prepared in a six‐step synthetic procedure starting from acyclic compounds, and shows good properties (detonation velocity DC–J = 8486 m s–1, detonation pressure pC–J = 302 kbar), and sensitivity toward mechanical stimuli. Compound 8 and its precursor (7, 3,5‐dimethoxy‐4,6‐dinitropyridazine‐1‐oxide) were characterized by means of multinuclear (1H, 13C, 14N, 15N) NMR spectroscopy, mass spectrometry, vibrational spectroscopy (IR and Raman), elemental analysis and differential thermal analysis (DTA) measurements. Compounds 4, 5, 6, 7, 8 and 9 were also characterized by low‐temperature single‐crystal X‐ray diffraction. The heats of formation for 7 and 8 were calculated using the atomization method based on CBS‐4M enthalpies. Using the experimentally determined (X‐ray) densities and the calculated standard molar enthalpies of formation, several detonation parameters such as the detonation pressure, energy and velocity were predicted by using the EXPLO5 code (V6.03). The sensitivities of 3,5‐dimethoxy‐4,6‐dinitropyridazine‐1‐oxide (7) and 3,5‐diamino‐4,6‐dinitropyridazine‐1‐oxide (8) toward impact, friction and electrical discharge were tested according to BAM standards. In addition, the shock reactivity of 8 was measured by applying the small‐scale shock reactivity test, showing similar values to HNS, PYX and TKX‐55.

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Energetic 1,2,5‐Oxadiazolo‐Pyridazine and its N‐Oxide

Cited by 31 publications

References 47 publications

Efficient Synthesis of a Superior Heat-Resistant Energetic Material Based on Fused Pyrazolotriazine Ring

Efficient Synthesis of a Superior Heat-Resistant Energetic Material Based on Fused Pyrazolotriazine Ring

Energetic 1H-Imidazo[4,5-d]pyridazine-2,4,7-triamine: A Novel Nitrogen-rich Fused Heterocyclic Cation with High Density

Energetic Functionalization of the Pyridazine Scaffold: Synthesis and Characterization of 3,5‐Diamino‐4,6‐dinitropyridazine‐1‐Oxide

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