4,4'-Dinitro-3,3'-diazenofuroxan

4,4’-Dinitro-3,3’-diazenofuroxan (DDF) is a powerful experimental high explosive with performance comparable to that of other high-density high-explosives such as octanitrocubane. It is synthesised by oxidative coupling of 4-amino-3-(azidocarbonyl)furoxan followed by Curtius rearrangement and further oxidation.[1][2]

4,4'-Dinitro-3,3'-diazenofuroxan
Names
IUPAC name
(E)-4-Nitro-N-[(E)-(4-nitro-2-oxo-1,2,5-oxadiazol-2-ium-3-ylidene)amino]-2-oxido-1,2,5-oxadiazol-3-imine
Other names
  • DDF
  • 4,4’-dinitro-3,3’-diazenofuroxan
  • bis(4-nitro-5-oxido-1,2,5-oxadiazol-5-ium-3-yl)diazene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4N8O8/c13-9(14)3-1(7-19-11(3)17)5-6-2-4(10(15)16)12(18)20-8-2
    Key: OWPQEEJZQLEILY-UHFFFAOYSA-N
  • C1(=NO[N+](=C1[N+](=O)[O-])[O-])N=NC2=NO[N+](=C2[N+](=O)[O-])[O-]
Properties
C4N8O8
Molar mass 288.092 g/mol
Density 2.02 g/cm3
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly Explosive
Explosive data
Detonation velocity 10,000 m/s
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

References
  1. Blinnikov AN, Kulikov AS, Makhova NN, Ovchinnikov IV, Pivina TS (1999). 4-Amino-3-azidocarbonyl Furoxan as an Universal Synthon for the Synthesis of Energetic Compounds of the Furoxan Series. 30th International Annual Conference of ICT. Karlsruhe, Germany. pp. 58/1–58/10.
  2. Agrawal JP, Hodgson RD (2007). Organic Chemistry of Explosives. John Wiley & Sons Ltd. p. 303. ISBN 978-0-470-02967-1.
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