Octafluorocubane

Octafluorocubane or perfluorocubane is an organofluorine compound with the formula C₈F₈, consisting of eight carbon atoms joined into a cube, with a fluorine bonded to each carbon corner. It is a colorless, sublimable solid at room temperature. It has been of longstanding theoretical interest, but was not synthesised until 2022, when it was prepared in several steps from a cubane carboxylic ester beginning with its heptafluorination. According to X-ray crystallography, the C-C distances (1.570 Å) in octafluorocubane are identical in length to those in the parent cubane (1.572 Å).^[1]

Octafluorocubane

Names
IUPAC name 1,2,3,4,5,6,7,8-octafluorocubane
Other names perfluorocubane
Identifiers
CAS Number	623570-55-8 Y
3D model (JSmol)	Interactive image
ChemSpider	20578010
PubChem CID	16746787
CompTox Dashboard (EPA)	DTXSID901171772
InChI InChI=1S/C8F8/c9-1-2(10)5(13)3(1,11)7(15)4(1,12)6(2,14)8(5,7)16 Key: DLEOOIAXKVODBG-UHFFFAOYSA-N
SMILES C12(C3(C4(C1(C5(C2(C3(C45F)F)F)F)F)F)F)F
Properties
Chemical formula	C8F8
Molar mass	248.075 g·mol−1
Appearance	colorless, sublimable
Density	2.429 g/cm3
Melting point	160.1–171.1 °C (320.2–340.0 °F; 433.2–444.2 K)
Related compounds
Related compounds	Octanitrocubane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Octafluorocubane has attracted interest from theorists because of its unusual electronic structure,^[2] which is indicated by its susceptibility to undergo reduction to a detectable anion C
₈F⁻
₈, with the free electron trapped inside of the cube.^[3]

The compound was voted "favorite molecule of 2022" by readers of Chemical & Engineering News.^[4]