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)	Interactive image
PubChem CID	89415335 15333368
SMILES C1(=NO[N+](=C1[N+](=O)[O-])[O-])N=NC2=NO[N+](=C2[N+](=O)[O-])[O-]
Properties
Chemical formula	C4N8O8
Molar mass	288.092 g/mol
Density	2.02 g/cm^3
Hazards
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

• 3,3′‐Diamino‐4,4′‐azoxyfurazan (DAAF)
• 2,4,6-Tris(trinitromethyl)-1,3,5-triazine
• ONC
• Hexanitrohexaazaisowurtzitane
• HNC
• HHTDD

References

1. Blinnikov AN, Kulikov AS, Makhova NN, Ovchinnikov IV, Pivina TS. 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, 1999. 58/1–58/10.
2. Agrawal JP, Hodgson RD. Organic Chemistry of Explosives. John Wiley & Sons Ltd, 2007. p303. ISBN 978-0-470-02967-1