Dodecahedrane

Dodecahedrane
Names
	IUPAC names (C20-Ih)[5]fullerane; hexadecahydro-1,6,5,2,4,3-(epibutane[1,1,2,3,4,4]hexayl)dipentaleno[2,1,6-gha:2′,1′,6′-cde]pentalene
	Systematic IUPAC name undecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]icosane
Identifiers
CAS Number	4493-23-6 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1880116
ChEBI	CHEBI:33013 ;
ChemSpider	109833 ;
Gmelin Reference	1326921
PubChem CID	123218;
UNII	FBO87C776P ;
CompTox Dashboard (EPA)	DTXSID90196340 ;
	InChI InChI=1S/C20H20/c1-2-5-7-3(1)9-10-4(1)8-6(2)12-11(5)17-13(7)15(9)19-16(10)14(8)18(12)20(17)19/h1-20H Key: OOHPORRAEMMMCX-UHFFFAOYSA-N ; InChI=1/C20H20/c1-2-5-7-3(1)9-10-4(1)8-6(2)12-11(5)17-13(7)15(9)19-16(10)14(8)18(12)20(17)19/h1-20H Key: OOHPORRAEMMMCX-UHFFFAOYAM;
	SMILES C12C3C4C5C1C6C7C2C8C3C9C4C1C5C6C2C7C8C9C12; C31C%10C2C5C%11C6C8C(C1C9C4C7C(C2C34)C5C6C7C89)C%10%11;
Properties
Chemical formula	C20H20
Molar mass	260.380 g·mol−1
Melting point	430±10°C
Related compounds
Related hydrocarbons	Cubane; Tetrahedrane; Pagodane (an isomer of dodecahedrane); Prismane
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dodecahedrane is a chemical compound, a hydrocarbon with formula C₂₀H₂₀, whose carbon atoms are arranged as the vertices (corners) of a regular dodecahedron. Each carbon is bound to three neighbouring carbon atoms and to a hydrogen atom. This compound is one of the three possible Platonic hydrocarbons, the other two being cubane and tetrahedrane.

Dodecahedrane does not occur in nature and has no significant uses. It was synthesized by Leo Paquette in 1982, primarily for the "aesthetically pleasing symmetry of the dodecahedral framework".^[2]

For many years, dodecahedrane was the simplest real carbon-based molecule with full icosahedral symmetry. Buckminsterfullerene (C₆₀), discovered in 1985, also has the same symmetry, but has three times as many carbons and 50% more atoms overall. The synthesis of the C₂₀ fullerene C₂₀ in 2000, from brominated dodecahedrane,^[3] may have demoted C₂₀H₂₀ to second place.

^ Lindberg, Thomas (2012-12-02). Strategies and Tactics in Organic Synthesis. ISBN 9780323152938.
^ Cite error: The named reference paquette1982 was invoked but never defined (see the help page).
^ Cite error: The named reference prinz2000 was invoked but never defined (see the help page).

[1] Lindberg, Thomas (2012-12-02). Strategies and Tactics in Organic Synthesis. ISBN 9780323152938.

[paquette1982-2] Cite error: The named reference paquette1982 was invoked but never defined (see the help page).

[prinz2000-3] Cite error: The named reference prinz2000 was invoked but never defined (see the help page).

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