Octanitrocubane

Octanitrocubane (molecular formula: C₈(NO₂)₈) is a proposed high explosive that, like TNT, is shock-insensitive (not readily detonated by shock).^[1] The octanitrocubane molecule has the same chemical structure as cubane (C₈H₈) except that each of the eight hydrogen atoms is replaced by a nitro group (NO₂). As of 1998, octanitrocubane had not been produced in quantities large enough to test its performance as an explosive.^[2]

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Octanitrocubane

Names
Preferred IUPAC name Octanitrocubane
Identifiers
CAS Number	99393-63-2 Y
3D model (JSmol)	Interactive image
ChemSpider	9937054 Y
PubChem CID	11762357
CompTox Dashboard (EPA)	DTXSID60471974
InChI InChI=1S/C8N8O16/c17-9(18)1-2(10(19)20)5(13(25)26)3(1,11(21)22)7(15(29)30)4(1,12(23)24)6(2,14(27)28)8(5,7)16(31)32 Y Key: URIPDZQYLPQBMG-UHFFFAOYSA-N Y InChI=1/C8N8O16/c17-9(18)1-2(10(19)20)5(13(25)26)3(1,11(21)22)7(15(29)30)4(1,12(23)24)6(2,14(27)28)8(5,7)16(31)32 Key: URIPDZQYLPQBMG-UHFFFAOYAW
SMILES [O-][N+](=O)C12C3([N+]([O-])=O)C4([N+]([O-])=O)C1([N+]([O-])=O)C5([N+]([O-])=O)C2([N+]([O-])=O)C3([N+]([O-])=O)C45[N+]([O-])=O
Properties
Chemical formula	C8N8O16
Molar mass	464.128 g·mol−1
Appearance	White solid
Density	1.979 g/cm3
Melting point	200 °C (392 °F; 473 K) (sublimes)
Solubility	Slightly soluble in hexane, soluble in ethanol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Explosive compound
Explosive data
Shock sensitivity	Low
Friction sensitivity	Low
Detonation velocity	10,100 m/s
Related compounds
Related compounds	Cubane Heptanitrocubane Octafluorocubane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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It is, however, not as powerful an explosive as once thought, as the high-density theoretical crystal structure has not been achieved. For this reason, heptanitrocubane, the slightly less nitrated form, is believed to have marginally better performance, despite having a worse oxygen balance.

Octanitrocubane is thought to have 20–25% greater performance than HMX (octogen). This increase in power is due to its highly expansive breakdown into CO₂ and N₂, as well as to the presence of strained chemical bonds in the molecule which have stored potential energy. In addition, it produces no water vapor upon combustion, making it less visible, and both the chemical itself and its decomposition products (nitrogen and carbon dioxide) are considered to be non-toxic.

Octanitrocubane was first synthesized by Philip Eaton (who was also the first to synthesize cubane in 1964) and Mao-Xi Zhang at the University of Chicago in 1999, with the structure proven by crystallographer Richard Gilardi of the United States Naval Research Laboratory.^[3][4]