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Bis(1,2,4-oxadiazolyl) Furoxan: A Promising Melt-Castable Eutectic Material of Low Sensitivity

Journal Article · · ChemPlusChem
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  1. US Army Research Lab., Aberdeen Proving Ground, MD (United States)
  2. U.S. Army Research LaboratoryEnergetic Materials Science Branch Aberdeen Proving Ground, MD 21005 USA
  3. Univ. of Maryland, College Park, MD (United States)
  4. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
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A scalable synthesis of bis(1,2,4-oxadiazoyl) furoxan, C6H2N6O4, its physical properties, and its theoretical performance values are described herein. Previous attempts to synthesize this compound required expensive reagents, and/or time-consuming synthesis processes and low overall yields. In addition to disclosing a streamlined synthesis of bis(1,2,4-oxadiazolyl) furoxan, we report its molecular configuration and crystal structure, as well as its correct melting point. Bis(1,2,4-oxadiazolyl) furoxan exhibits a very insensitive behavior to impact, friction, and electrostatic discharge, with a calculated detonation pressure 20 % higher than that of TNT. Given its physical properties and theoretical performance values, this material can be classified as a promising ingredient in the development of melt-castable eutectic technology.
Research Organization:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Organization:
US Army; USDOE National Nuclear Security Administration (NNSA), Office of Defense Programs (DP)
Grant/Contract Number:
89233218CNA000001
OSTI ID:
1768532
Report Number(s):
LA-UR--18-30932
Journal Information:
ChemPlusChem, Journal Name: ChemPlusChem Journal Issue: 4 Vol. 84; ISSN 2192-6506
Publisher:
ChemPubSoc EuropeCopyright Statement
Country of Publication:
United States
Language:
English

References (23)

Combination of 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Moieties for the Generation of High-Performance Energetic Materials journal June 2015
Combination of 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Moieties for the Generation of High-Performance Energetic Materials journal June 2015
3,3′-Bi(1,2,4-oxadiazoles) Featuring the Fluorodinitromethyl and Trinitromethyl Groups journal May 2014
Synthesis of Biisoxazoletetrakis(methyl nitrate): A Potential Nitrate Plasticizer and Highly Explosive Material: Synthesis of Biisoxazoletetrakis(methyl nitrate): A Potential Nitrate Plasticizer and Highly Explosive Material journal April 2017
Evaluation of electrostatic descriptors for predicting crystalline density journal June 2013
Desilylative nitration of C,N -disilylated 3-amino-4-methylfurazan journal September 2005
Review on Melt Cast Explosives journal October 2011
Synthesis of the amides and acid halides of 1,2,4-oxadiazole-3-carbohydroxamic acid journal April 1994
Chemistry of dinitroacetonitrile—I journal January 1962
The first metal complexes of 3,3′-bi-1,2,4-oxadiazole: A curiously ignored ligand journal August 2007
Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient journal May 2018
Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations journal January 2006
Accurate Predictions of Crystal Densities Using Quantum Mechanical Molecular Volumes journal October 2007
Searching for Low-Sensitivity Cast-Melt High-Energy-Density Materials: Synthesis, Characterization, and Decomposition Kinetics of 3,4-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-2-oxide journal February 2015
Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations journal May 2009
A Comparison of Methods To Predict Solid Phase Heats of Formation of Molecular Energetic Salts journal January 2009
5,5′-Bis-(trinitromethyl)-3,3′-bi-(1,2,4-oxadiazole): a stable ternary CNO-compound with high density journal January 2014
Energetic alliance of tetrazole-1-oxides and 1,2,5-oxadiazoles journal January 2015
Efficient assembly of mono- and bis(1,2,4-oxadiazol-3-yl)furoxan scaffolds via tandem reactions of furoxanylamidoximes journal January 2015
Exploiting the energetic potential of 1,2,4-oxadiazole derivatives: combining the benefits of a 1,2,4-oxadiazole framework with various energetic functionalities journal January 2017
Boosting energetic performance by trimerizing furoxan journal January 2018
Crystal structure refinement with SHELXL journal January 2015
SHELXT – Integrated space-group and crystal-structure determination journal January 2015

Cited By (2)

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance journal November 2019
Synthesis and comparison of copper( ii ) complexes with various N -aminotetrazole ligands involving trinitrophenol anions journal January 2019

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
energetic materials
eutectic technology
explosives
heterocycles
organic synthesis