Hydrogen halides as nucleophilic agents for 3,4,5-trinitro-1H-pyrazoles

Далингер, И. Л.; Вацадзе, И. А.; Шкинева, Т. К.; Popova, G. P.; Шевелев, С. А.

doi:10.1016/j.mencom.2012.01.017

Cited by 21 publications

(18 citation statements)

References 11 publications

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“…This same conclusion was also suggested from an earlier study. [14] Pure di(3,5-dinitro-4-chloropyrazole) (5) or di(3,4dinitro-5-chloropyrazole)-N-nitromethanamine (7) were dissolved in DMSO and treated with an excess of sodium azide. After one hour, when the reactions were complete, the residues were washed with water and dichloromethane to give 8 and 9 in high yields, 92 and 89 %, respectively.…”

Section: Resultsmentioning

confidence: 99%

Nitramines with Varying Sensitivities: Functionalized Dipyrazolyl‐ N‐nitromethanamines as Energetic Materials

Zhang

Parrish

et al. 2013

Chemistry A European J

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1,3-Dichloro-2-nitro-2-azapropane is an excellent precursor to dense energetic functionalized dipyrazolyl-N-nitromethanamines. This new family of energetic compounds was fully characterized by using (1)H, (13)C, and (15)N NMR and IR spectroscopy, differential scanning calorimetry, elemental analysis, and impact sensitivity tests. Additionally, single-crystal X-ray structuring was done for 3 and 5·CH3CN, which gave insight into structural characteristics. The experimentally determined densities of 2-9 fall between 1.69 and 1.90 g cm(-3). Heats of formation and detonation properties were calculated by using Gaussian 03 and EXPLO5 programs, respectively. The influence of different energetic moieties on the structural and energetic properties was established theoretically.

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Section: Resultsmentioning

confidence: 99%

Nitramines with Varying Sensitivities: Functionalized Dipyrazolyl‐ N‐nitromethanamines as Energetic Materials

Zhang

Parrish

et al. 2013

Chemistry A European J

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“…Compound 1 was prepared by modification of the known methods. 10,12,13 1Hpyrazole (1.00 g, 14.7 mmol) and N-chlorosuccinimide (NCS, 2.00 g, 15.0 mmol) were added to dichloromethane (CH 2 Cl 2 , 15 mL) and stirred at room temperature for 12 h. The reaction mixture was then filtered and the filtered solid was washed several times with CH 2 Cl 2 . The filtrate was washed with water (3 × 10 mL) in an extraction funnel and dried over MgSO 4 .…”

Section: Methodsmentioning

confidence: 99%

“…4-Chloro-3,4-dinitro-1H-pyrazole (1, ClDNP, Scheme 1) is an attractive explosive precursor because it can be obtained just in one-step reaction of 4-chloro-pyrazole with a mixed acid of nitric and sulfuric acid. 12 However, its N, N 0 -methylene bridged compound has not been reported due to the low nucleophilicity of 1. Instead, more nucleophilic 4-aminodinitropyrazole was used to give the corresponding N,N 0 -methylene bridged bis(dinitropyrazole) due to the electron-donating amino group.…”

Section: Introductionmentioning

confidence: 99%

Bis(4‐azido‐3,5‐dinitro‐1H‐pyrazol‐1‐yl)methane as a New Green Primary Explosive

Kim

Lee

Shin

et al. 2020

Bulletin Korean Chem Soc

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Bis(4-chloro-3,5-dinitro-1H-pyrazol-1-yl)methane 2 was obtained for the first time via the coupling reaction of 4-chloro-3,5-dinitro-1H-pyrazole 1 as a promising precursor for new explosives. The careful selection of the reaction conditions enabled the coupling of 1 having the poor reactivity to produce 2 in a good yield. The target compound, bis(4-azido-3,5-dinitro-1H-pyrazol-1-yl)methane 3, was produced by the double azidation reaction of 2 in one step. Some explosive properties of 2 and 3 were characterized and 3 is expected to be a novel green primary explosive having superior explosive properties and better thermal stability than those of a widely used primary explosive, 2-diazo-4,6-dinitrophenol .

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“…[22,29] A subsequent nitration using a mixture of sulfuric acid and fuming nitric acid formed 4chloro-3,5-dinitropyrazole. [22,30,31] The third step was performed in an steel autoclave using aqueous ammonia to yield 4-amino-3,5-dinitropyrazole (ADNP, 1). [22,30,31] ADNP was diazotated in diluted sulfuric acid using sodium nitrite.…”

Section: Synthesismentioning

confidence: 99%

“…[22,30,31] The third step was performed in an steel autoclave using aqueous ammonia to yield 4-amino-3,5-dinitropyrazole (ADNP, 1). [22,30,31] ADNP was diazotated in diluted sulfuric acid using sodium nitrite. After neutralization with sodium carbonate the in situ generated diazonium group was substituted by cyanide by an reductive elimination reaction to form 4-cyano-3,5-dinitropyrazole (2) as sodium salt.…”

Section: Synthesismentioning

confidence: 99%

Combining Performance with Thermal Stability: Synthesis and Characterization of 5‐(3,5‐Dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its Energetic Derivatives

Benz

Klapötke

Stierstorfer

2020

Zeitschrift anorg allge chemie

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In this study, we present the synthesis of 5‐(3,5‐dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its energetic derivatives starting from 4‐amino‐3,5‐dinitropyrazole, which was diazotized and cyanide substituted. A subsequent cycloaddition reaction with sodium azide led to 5‐(3,5‐dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole (3). Several alkaline metal and nitrogen‐rich salts were prepared and characterized by low‐temperature X‐ray diffraction. Additionally, all compounds were analyzed by vibrational spectroscopy (IR), 1H, 13C and 14N NMR spectroscopy, elemental analysis and differential thermal analysis (DTA). Additionally, the heats of formation for selected compounds were calculated using the atomization method based on CBS‐4M enthalpies as well as important detonation parameters by using the EXPLO5 code (V6.05). Furthermore, the sensitivities of 3 and all synthesized salts toward friction, impact and electrostatic discharge according to BAM (Bundesamt für Materialforschung) were determined and compared to RDX.

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Hydrogen halides as nucleophilic agents for 3,4,5-trinitro-1H-pyrazoles

Cited by 21 publications

References 11 publications

Nitramines with Varying Sensitivities: Functionalized Dipyrazolyl‐ N‐nitromethanamines as Energetic Materials

Nitramines with Varying Sensitivities: Functionalized Dipyrazolyl‐ N‐nitromethanamines as Energetic Materials

Bis(4‐azido‐3,5‐dinitro‐1H‐pyrazol‐1‐yl)methane as a New Green Primary Explosive

Combining Performance with Thermal Stability: Synthesis and Characterization of 5‐(3,5‐Dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its Energetic Derivatives

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