An improved synthesis of 5-amino-3-nitro-1<i>H</i>-1,2,4-triazole (ANTA), a useful intermediate for the preparation of insensitive high explosives

Lee, K.-Y.; Storm, Carlyle B.; Hiskey, Michael A.; Coburn, Michael D.

doi:10.1080/07370659108019382

Cited by 106 publications

(41 citation statements)

References 3 publications

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“…Lee et al [68] reported the preparation of 3-amino-5-nitro-1,2,4-triazole by an improved sequence where the dinitrotriazole salt was reduced with hydrazine, giving an almost quantitative conversion. The general interest in ANTA is because of amino-nitroheterocyclic compound as insensitive energetic material.…”

Section: Insensitive High Explosives Based On Heterocyclic Nucleimentioning

confidence: 99%

A review of advanced high performance, insensitive and thermally stable energetic materials emerging for military and space applications

Sikder

2004

Journal of Hazardous Materials

735

363

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Section: Insensitive High Explosives Based On Heterocyclic Nucleimentioning

confidence: 99%

A review of advanced high performance, insensitive and thermally stable energetic materials emerging for military and space applications

Sikder

2004

Journal of Hazardous Materials

735

363

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“…[14][15][16] Tetrazole-based energetic materials seem to show the best compromise between high heats of formation and good thermal stabilities. On the other hand, the presence of one carbon atom in the ring limits the introduction of functionality, whereas triazole-based energetic materials can be much more readily derivatised, for example, to the dinitro [17] diamino [18] or diazido [19] compounds; the presence of two carbon atoms allows the easy introduction and/or combination of two of the aforementioned highly endothermic functional groups, allowing the formation of compounds with high positive heats of formation (i.e., high performances). Among others, triazolium-based energetic materials have found use as high explosives, [20] gas generators [21] and ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Darwich

Klapötke

Sabaté

2008

Chemistry A European J

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3,4,5-Triamino-1,2,4-triazole (guanazine, 1) can be readily methylated with methyl iodide yielding methylguanazinium iodide (2). Salts containing the novel methylguanazinium cation with energetic anions were synthesised by metathesis reactions with silver azide (3), silver nitrate (4), silver perchlorate (5), sodium 5,5'-azotetrazolate (6), silver 5-nitrotetrazolate (7) and silver dinitramide (8), yielding a new family of heterocycle-based salts, which were fully characterised by analytical (mass spectrometry and elemental analysis) and spectroscopic methods (IR, Raman and NMR). In addition, the molecular structures of all compounds were confirmed by X-ray analysis, revealing extensive hydrogen-bonding in the solid state and densities between 1.399 (3) and 1.669 g cm(-3) (5). The hydrogen-bonded ring motifs are discussed in the formalism of graph-set analysis for hydrogen-bond patterns and compared to each other. Preliminary sensitivity testing of the crystalline compounds indicate surprisingly low sensitivities to both friction and impact, the highest friction and shock sensitivity being found for the perchlorate (5, 220 N) and the dinitramide (8, 20 J) salts, respectively. In addition, DSC analysis was used to assess the thermal stabilities of the compounds: 3-6 melt above 200 degrees C with concomitant decomposition, whereas 7 and 8 have clearly defined melting points at 162 and 129 degrees C, respectively, and with decomposition occurring about 30 degrees C above the melting point. Lastly all compounds have positive calculated heats of formation between 336 (4) and 4070 kJ kg(-1) (6) and calculated detonation velocities in the range between 8330 (7) and 8922 m s(-1) (6) making them of interest as new highly energetic materials with low sensitivity.

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“…3-Amino-5-nitro-1,2,4-triazole (ANTA), an insensitive high explosive (IHE) similar to TATB, has potential as a more energetic alternative to NTO [37] and meets all the above criteria. Furthermore, ANTA had also been proposed by Naval Research Laboratory (NRL), USA to evaluate it as a potential IHE for nuclear weapons applications [38]. More recently, with the development of new energetic materials, Professor Klapotke and his coworkers have researched several heterocyclic ring systems and reported the synthesis, characterization, and the energetic properties of compounds belonging to a new class of energetic materials, including trinitroethyl-substituted compounds, derivatives of 1,5-diamino-1H-tetrazole and 1,5-diamino-4-methyltetrazolium dinitramide [39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Investigation of correlation between impact sensitivities and bond dissociation energies in some triazole energetic compounds

Zhao

Cheng

2010

Struct Chem

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In this article, density functional theory has been utilized to study on the correlation between impact sensitivities h 50% and the bond dissociation energies (BDEs) of nine triazole energetic explosives. By employing B3LYP and B3P86 method with the 6-311G** basis set, all the molecules have been fully optimized. The BDEs for removal of the NO 2 group in these compounds have also been calculated at the same level. Computed results show that BDEs calculated by B3LYP method are all less than those by B3P86 method. The relationship between the impact sensitivities and the weakest C-NO 2 bond dissociation energy (BDE) values have been investigated.The results indicate a good linear correlation between the impact sensitivity h 50% and the ratio (BDE/E) of the weakest BDE to the total energy E.

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An improved synthesis of 5-amino-3-nitro-1H-1,2,4-triazole (ANTA), a useful intermediate for the preparation of insensitive high explosives

Cited by 106 publications

References 3 publications

A review of advanced high performance, insensitive and thermally stable energetic materials emerging for military and space applications

A review of advanced high performance, insensitive and thermally stable energetic materials emerging for military and space applications

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Investigation of correlation between impact sensitivities and bond dissociation energies in some triazole energetic compounds

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