ChemInform Abstract: Synthesis and Some Reactions of 5‐Substituted 1,2,4‐Triazolyl‐3‐acetic Acid (III).

Kofman, T. P.; Uvarova, T. A.; Kartseva, G. Yu.

doi:10.1002/chin.199607148

Cited by 2 publications

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“…Compounds such as aminotriazolylacetic acids, for example, 4 and 5 , give the corresponding polynitro compounds by nitration with mixed acids. Aminotriazolylacetic acid ( 4 ) was synthesized by intramolecular condensation of the malonyl derivative of aminoguanidine bicarbonate in alkaline medium (Scheme ) …”

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confidence: 99%

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Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties

2011

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Various new polynitro-1,2,4-triazoles containing a trinitromethyl group were synthesized by straightforward routes. These high nitrogen and oxygen-rich compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, natural bonding orbital (NBO) analysis, and differential scanning calorimetry (DSC) and, in the case of 12, with single crystal X-ray structuring. The heats of formation for all compounds were calculated with Gaussian 03 (revision D.01) and then combined with experimentally determined densities to determine detonation pressures (P) and velocities (D) of the energetic materials (Cheetah 5.0). They exhibit high density, good thermal stability, acceptable oxygen balance, positive heat of formation, and excellent detonation properties, which, in some cases, are superior to those of TNT, RDX, and HMX.

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Section: Resultsmentioning

confidence: 99%

“…In all of these cases, low yields of the impure methylated product ( 12 ) were obtained. When tetranitro 9 was reacted with commercially available trimethylsilyl diazomethane, 1-methyl-5-trinitro-3-trinitromethyl-1 H -[1,2,4]triazole ( 12 ) was obtained in 80% yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties

2011

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“…Nitration using mixed acids produced trinitromethyl triazole 3 . Similarly, the azo-compound 4 , which was prepared by reacting aminotriazole 1 with potassium permanganate, was converted to the corresponding trinitromethyl compound 5 by mixed acid nitration (Scheme ). , …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Promising Properties of a New Family of High-Density Energetic Salts of 5-Nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5′-Bis(trinitromethyl)-3,3′-azo-1H-1,2,4-triazole

2011

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Salts of trinitromethyl-substituted triazoles, 5-nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5'-bis(trinitromethyl)-3,3'-azo-1H-1,2,4-triazole (5), form a new class of highly dense energetic materials. Single-crystal X-ray structuring supports the formation of the cocrystal of 5 with 3,5-diamino-1,2,4-triazole, which was found to be remarkably less impact-sensitive than the azo precursor. The compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry. Based on heats of formation calculated with Gaussian 03 and combined with experimentally determined densities, detonation properties of the energetic materials obtained with the EXPLO5 program identify them as potentially explosive compounds. They exhibit high density, moderate to good thermal stability, acceptable oxygen balance, reasonable heat of formation, and excellent detonation properties, which in some cases are superior to those of 1,3,5,-trinitrotriazacyclohexane (RDX).

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ChemInform Abstract: Synthesis and Some Reactions of 5‐Substituted 1,2,4‐Triazolyl‐3‐acetic Acid (III).

Cited by 2 publications

References 0 publications

Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties

Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties

Synthesis and Promising Properties of a New Family of High-Density Energetic Salts of 5-Nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5′-Bis(trinitromethyl)-3,3′-azo-1H-1,2,4-triazole

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