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Title: An Energetic Triazolo-1,2,4-Triazine and its N-Oxide

Journal Article · · Angewandte Chemie (International Edition)
 [1];  [2];  [2];  [3];  [3]
  1. Nalas Engineering, Inc., Centerbrook, CT (United States)
  2. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
  3. Naval Research Lab. (NRL), Washington, DC (United States)
+ Show Author Affiliations

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 occurred to produced 4- amino-3,7-dinitrotriazolo-[5,1-c][1,2,4] triazine (DPX-26). X-ray crystallographic analysis shows that the DPX-26 has a density of 1.86 g/cm3 while it is calculated to have a heat of formation of 398.3 kJ/mol. 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), and is also predicted to be a high performance material with enhanced safety properties.

Research Organization:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
89233218CNA000001
OSTI ID:
1501802
Report Number(s):
LA-UR-16-25231
Journal Information:
Angewandte Chemie (International Edition), Vol. 55, Issue 49; ISSN 1433-7851
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 129 works
Citation information provided by
Web of Science

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Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability journal June 2017
Azido and Tetrazolo 1,2,4,5-Tetrazine N-Oxides journal February 2017
The Chemistry and Properties of Energetic Materials Bearing [1,2,4]Triazolo[4,3- b ][1,2,4,5]tetrazine Fused Rings journal October 2018
Nitramino- and Dinitromethyl-Substituted 1,2,4-Triazole Derivatives as High-Performance Energetic Materials journal June 2017
Synthesis and Characterization of 2,2′-Dinitramino-5,5′-bi(1-oxa-3,4-diazole) and Derivatives as Economic and Highly Dense Energetic Materials journal July 2017
Energetic 1,2,5-Oxadiazolo-Pyridazine and its N-Oxide journal October 2017
Methylsemicarbazide as a Ligand in Late 3d Transition Metal Complexes journal January 2018
Synthesis and Characterization of 4-(1,2,4-Triazole-5-yl)furazan Derivatives as High-Performance Insensitive Energetic Materials journal June 2018
Synthesis, Characterization, and Properties of Energetic Compounds Based on a CH 2 -Bridged Dinitromethyl Explosophore : Synthesis, Characterization, and Properties of Energetic Compounds Based on a CH journal January 2018
Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine: Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine journal May 2018
An Energetic (Nitro- NNO -azoxy)triazolo-1,2,4-triazine : An Energetic (Nitro- journal June 2019
High Density of a New Fused Heterocycle: 7,8-Dinitro-4-oxo-4,6-dihydropyrazolo[5, 1-d][1, 2,3,5]tetrazine 2-oxide and Its Energetic Salts journal May 2018
Nitrogen-rich Salts based on 3-Dinitromethyl-[1,2,4]triazine: Synthesis, Characterization, and Performance: Nitrogen-rich Salts based on 3-Dinitromethyl-[1,2,4]triazine: Synthesis, Characterization, and Performance journal August 2019
Accelerating the discovery of insensitive high-energy-density materials by a materials genome approach journal June 2018
New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan journal March 2019
Synthetic manifestation of nitro substituted tetrazole-N-(hetero)aryl derivatives and energetic studies journal January 2017
Metal salts and complexes of 1,1′-dinitramino-5,5′-bitetrazole journal January 2017
Alkali and alkaline earth metal salts of tetrazolone: structurally interesting and excellently thermostable journal January 2017
5,6-Di(2-fluoro-2,2-dinitroethoxy)furazano[3,4-b]pyrazine: a high performance melt-cast energetic material and its polycrystalline properties journal January 2017
Reaction mechanisms and sensitivity of silicon nitrocarbamate and related systems from quantum mechanics reaction dynamics journal January 2018
A C–C bonded 5,6-fused bicyclic energetic molecule: exploring an advanced energetic compound with improved performance journal January 2018
Polycyclic N -oxides: high performing, low sensitivity energetic materials journal January 2019
Theoretical investigations on azole-fused tricyclic 1,2,3,4-tetrazine-2-oxides journal January 2018
Fused rings with N -oxide and –NH 2 : good combination for high density and low sensitivity energetic materials journal January 2019
5,6-Fused bicyclic tetrazolo-pyridazine energetic materials journal January 2020
From BTO 2− to HBTO − insensitive energetic salt: a route to boost energy journal January 2019
Preparation of CL-20/TFAZ cocrystals under aqueous conditions: balancing high performance and low sensitivity journal January 2019
A facile synthesis of energetic salts based on fully nitroamino-functionalized [1,2,4]triazolo[4,3- b ][1,2,4]triazole journal January 2020
C 8 N 12 O 10 : a promising energetic compound with excellent detonation performance and desirable sensitivity journal January 2019
Synthesis of high-performance insensitive energetic materials based on nitropyrazole and 1,2,4-triazole journal January 2019
Stabilization of an intramolecular hydrogen-bond block in an s -triazine insensitive high-energy material journal January 2019
Nitramino-furazan-functionalized fused high-nitrogen backbones as energetic materials with high detonation performance and good molecular stabilities journal January 2019
Multipurpose [1,2,4]triazolo[4,3- b ][1,2,4,5] tetrazine-based energetic materials journal January 2019
Modification of crystalline energetic salts through polymorphic transition: enhanced crystal density and energy performance journal January 2020
Thermogravimetric analysis, kinetic study, and pyrolysis–GC/MS analysis of 1,1ʹ-azobis-1,2,3-triazole and 4,4ʹ-azobis-1,2,4-triazole journal March 2018
Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability journal June 2017

Linked Research (3)

Figures / Tables (6)

Scheme 1(p. 3)figure Scheme 1
Figure 1(p. 4)figure Figure 1
Figure 2(p. 4)figure Figure 2
Figure 3(p. 4)figure Figure 3
Figure 4(p. 5)figure Figure 4
Table 1(p. 5)table Table 1

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