Hexanitrohexaazaisowurtzitane

Hexanitrohexaazaisowurtzitane
IUPAC name 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane[citation needed]
Other names CL-20
Identifiers
Abbreviations	CL-20, HNIW
CAS number	135285-90-4 Y
PubChem	9889323, 11048432 (3R,9R)-dodec, 11419235 (3R,5S,9R,11S)- dodec
ChemSpider	8064994 Y, 9223599 (3R,9R)-dodec Y, 9594121 (3R,5S,9R,11S)- dodec Y
Jmol-3D images	Image 1 Image 2
SMILES o:n(:o)N1C2C3N(C4C(N3n(:o):o)N(C(C1N4n(:o):o)N2n(:o):o)n(:o):o)n(:o):o [O-][N+](=O)N1C2C3N(C4C(N3[N+]([O-])=O)N(C(C1N4[N+]([O-])=O)N2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
InChI InChI=1S/C6H6N12O12/c19-13(20)7-1-2-8(14(21)22)5(7)6-9(15(23)24)3(11(1)17(27)28)4(10(6)16(25)26)12(2)18(29)30/h1-6H Y Key: NDYLCHGXSQOGMS-UHFFFAOYSA-N Y
Properties
Molecular formula	C6N12H6O12
Molar mass	438.1850 g mol-1
Exact mass	438.022813716 g mol-1
Explosive data
Explosive velocity	9.38 km s-1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, also called HNIW, and CL-20, is a nitroamine explosive with the formula C₆H₆N₁₂O₁₂, developed by the China Lake facility, primarily to be used in propellants. It has a better oxidizer-to-fuel ratio than conventional HMX or RDX. It produces 20% more energy than traditional HMX-based propellants, and is widely superior to conventional high-energy propellants and explosives.

While most development of CL-20 has been fielded by the Thiokol Corporation, the US Navy (through ONR) has also been interested in CL-20 for use in rocket propellants, such as for missiles, as it has lower observability characteristics (e.g., less visible smoke).

CL-20 has not yet been fielded in any production weapons system, but is presently undergoing testing for stability, production capabilities, and other weapons characteristics.

Synthesis

It is made by reacting hexabenzylhexaazaisowurtzitane with acetic anhydride yielding dibenzyltetraethanoylhexaazaisowurtzitane, which is then reacted with nitronium tetrafluoroborate and nitrosonium tetrafluoroborate, resulting in HNIW.

See also

• 2,4,6-Tris(trinitromethyl)-1,3,5-triazine
• 4,4’-Dinitro-3,3’-diazenofuroxan (DDF)
• Heptanitrocubane (HNC)
• HHTDD
• Octanitrocubane (ONC)