Nitropyrazoles

Далингер, И. Л.; Vatsadse, Irina A.; Шкинева, Т. К.; Popova, G. P.; Уграк, Б. И.; Шевелев, С. А.

doi:10.1007/s11172-010-0287-9

Cited by 68 publications

(31 citation statements)

References 10 publications

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“…With selected cations, 14 nitrogen-rich energetic salts were synthesized in high yield by metathesis reactions. These salts were fully characterized by 1 H, 13 C NMR, and IR spectroscopy and elemental analysis. Additionally, the structures of the ammonium, 3,4,5-triaminotriazolium, and biguanidinium salts were confirmed by single-crystal X-ray diffraction.…”

Section: à3mentioning

confidence: 99%

“…[9] Among them, the pyrazole-based nitroazoles have been extensively investigated. In addition to 3,4,5-trinitropyrazole, [10,11] its dinitro-derivatives, such as 4-amino-3,5-dinitropyrazole, [12] 5-amino-3,4-dinotropyrazole, [11] 5-azo-3,4-dinitropyrazole, [11] 5-nitramino-3,4-dinitropyrazole, [13] have been reported. Based on our calculations, another dinitro-derivative of pyrazole (the unknown 4-nitramino-3,5-dinitropyrazole), with a calculated density of 1.97 g cm…”

Section: Introductionmentioning

confidence: 99%

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4‐Nitramino‐3,5‐dinitropyrazole‐Based Energetic Salts

Zhang

Parrish

Shreeve

2011

Chemistry A European J

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4-Nitramino-3,5-dinitropyrazole was prepared and stabilized through the formation of its ammonium salt. With selected cations, 14 nitrogen-rich energetic salts were synthesized in high yield by metathesis reactions. These salts were fully characterized by (1)H, (13)C NMR, and IR spectroscopy and elemental analysis. Additionally, the structures of the ammonium, 3,4,5-triaminotriazolium, and biguanidinium salts were confirmed by single-crystal X-ray diffraction. Based on experimental and calculated values, the 4-nitramino-3,5-dinitropyrazolate salts show properties, such as decomposition temperatures (115-229 °C), detonation pressures (23.27-37.42 GPa) and velocities (7713-9013 ms(-1)), and impact sensitivities (5-40 J) that place them with energetics such as RDX and TATB.

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Section: à3mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

4‐Nitramino‐3,5‐dinitropyrazole‐Based Energetic Salts

Zhang

Parrish

Shreeve

2011

Chemistry A European J

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“…[6][7][8][9] Higher performing explosives (HMX) have high density and better oxygen balance; in the cases of CL-20 and octanitrocubane, they have large positive heats-of-formation from their strained fused-ring/cage-like structures. 11 The fused-rings produce a at molecular geometry and p-p interactions. 11 The fused-rings produce a at molecular geometry and p-p interactions.…”

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confidence: 99%

“…15 We present an improved synthesis to ADNP from dinitro-pyrazole (DNP) by utilizing vicarious nucleophilic substitution (VNS) of the pyrazole C-H 16,17 as displayed in Scheme 1. 11 A few synthetic routes to ADNP have been reported 12 and involve the reduction of 5-azido-3,4-dinitropyrazole, 13,14 the Hofmann rearrangement of 3,4-dinitropyrazole carboxamide, 11 or substitution of N-protected 3,4,5-trinitropyrazoles.…”

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confidence: 99%

A high density pyrazolo-triazine explosive (PTX)

2015

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The fused-ring heterocycle 4-amino-3,7,8-trinitropyrazolo-[5,1-c] [1,2,4]triazine (PTX) has promising explosive properties. The Cheetah thermochemical code used its calculated standard enthalpy of formation and its measured crystal density of 1.946 g cm À3 to predict HMX-like explosive performance, while measurements of its thermal stability, sensitivity to impact, friction, and spark showed greater safety margins.

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“…[9] We have also investigated the density,e nthalpy, and safety properties of this compound. [9] We have also investigated the density,e nthalpy, and safety properties of this compound.…”

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confidence: 99%

An Energetic Triazolo‐1,2,4‐Triazine and its N‐Oxide

et al. 2016

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The reaction of 3-amino-5-nitro-1,2,4-triazole with nitrous acid produces the corresponding diazonium salt. When the diazonium salt is treated with nitroacetonitrile, a subsequent condensation and cyclization reaction occurres to produced 4-amino-3,7-dinitrotriazolo- [5,1-c][1,2,4] triazine (DPX-26). Xray crystallographic analysis shows that the DPX-26 has a density of 1.86 g cm À3 , while it is calculated to have a heat of formation of 398.3 kJ mol À1 . DPX-26 is predicted to approach the explosive performance of RDX but displays significantly better safety properties. Oxidation of DPX-26 using hypofluorous acid produces 4-amino-3,7-dinitrotriazolo-[5,1-c][1,2,4] triazine 4-oxide (DPX-27), which is also predicted to be a highperformance material with enhanced safety properties.Energetic materials, that is propellants, explosives, and pyrotechnics, have long attracted intense research efforts in the chemical sciences, including interest from early scientists such as Liebig, Berzelius, and Gay-Lussac. [1,2] Much as these foundational researchers focused on understanding the properties of new materials, todays energetic materials researchers strive to understand how to break the correlation between high-performance explosives and high sensitivity.[3] While there are some outlier energetic materials that do not follow this trend, [4] these materials have not yet reached the performance of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) while displaying the insensitivity of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB). Additionally, the ability to intentionally design such an outlier from first principles is still in its infancy.[5] Within our own laboratory, the rational design of new energetic materials with tailored sensitivity and performance has been a long-term objective. Within this context, a major goal in the field is the replacement of cyclotrimethylenetrinitramine (RDX) with a material that shows lower sensitivity and comparable or higher performance, and yet avoids toxicity and carcinogenicity.It is known that vicinal C-amino/C-nitro functionalities tend to lead to increased insensitivity through both inter-and intramolecular hydrogen bonding, as seen in the insensitive high explosive 1,3,5-triamino-2,4,6-trinitrobenzene (impact sensitivity > 40 J, friction sensitivity > 360 N, electrostatic discharge (ESD) sensitivity > 0.125 J).[6] 1,1-Diamino-2,2-dinitroethylene (FOX-7) is another example where vicinal amino and nitro groups combine to provide an energetic material with good performance (detonation velocity and pressure) and safety properties (impact sensitivity 15-20 J, friction sensitivity 340 N).[7] Recently, we began an investigation of other heterocyclic architectures incorporating vicinal amino and nitro groups. [8] In prior work, we developed an efficient synthesis of 4-amino-3,7,8-trinitropyrazolo-[5,1-c][1,2,4] triazine, which was originally synthesized by Dalinger and coworkers. [9] We have also investigated the density, enthalpy, and safety properties of this compound. From ...

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Nitropyrazoles

Cited by 68 publications

References 10 publications

4‐Nitramino‐3,5‐dinitropyrazole‐Based Energetic Salts

4‐Nitramino‐3,5‐dinitropyrazole‐Based Energetic Salts

A high density pyrazolo-triazine explosive (PTX)

An Energetic Triazolo‐1,2,4‐Triazine and its N‐Oxide

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