Cyclooctane

Cyclooctane

Identifiers
CAS Number	292-64-8 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL452651 Y
ChemSpider	8909 Y
ECHA InfoCard	100.005.484
PubChem	9266
InChI InChI=1S/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2 Y Key: WJTCGQSWYFHTAC-UHFFFAOYSA-N Y InChI=1/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2 Key: WJTCGQSWYFHTAC-UHFFFAOYAO
SMILES C1CCCCCCC1
Properties
Chemical formula	C8H16
Molar mass	112.21 g/mol
Density	0.834 g/cm3
Melting point	14.59 °C (58.26 °F; 287.74 K)
Boiling point	149 °C (300 °F; 422 K)
Solubility in water	7.90 mg/L
Magnetic susceptibility (χ)	-91.4·10−6 cm3/mol
Related compounds
Related cycloalkanes	Cycloheptane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Cyclooctane is a cycloalkane with the molecular formula (CH₂)₈. It is a simple colourless hydrocarbon, but it is often a reference compound for saturated eight-membered ring compounds in general.

The conformation of cyclooctane has been studied extensively using computational methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy." The boat-chair conformation I is the most stable form. This conformation was confirmed by Allinger and co-workers. The crown conformationII is slightly less stable. Among the many compounds exhibiting the crown conformation (structure II) is S₈, elemental sulfur.

The main route to cyclooctane derivatives involves the dimerization of butadiene, catalysed by nickel(0) complexes such as nickel bis(cyclooctadiene). This process affords, among other products, 1,5-cyclooctadiene (COD), which can be hydrogenated. COD is widely used for the preparation of precatalysts for homogeneous catalysis. The activation of these catalysts under H2, produces cyclooctane, which is usually discarded or burnt:

Cyclooctane participates in no reactions except those typical of other saturated hydrocarbons, combustion and free radical halogenation. Recent work on alkane functionalisation, using peroxides such as dicumyl peroxide, has opened up the chemistry to some extent, allowing for example the introduction of a phenylamino group.