Perfluorocyclohexane

Perfluorocyclohexane
Names
	IUPAC name 1,1,2,2,3,3,4,4,5,5,6,6-Dodecafluorocyclohexane
	Other names Dodecafluorocyclohexane, Cyclohexane, dodecafluoro-
Identifiers
CAS Number	355-68-0;
3D model (JSmol)	Interactive image;
ChemSpider	9263 ;
ECHA InfoCard	100.005.993
EC Number	206-591-3;
PubChem CID	9640;
CompTox Dashboard (EPA)	DTXSID5075232 ;
	InChI InChI=1S/C6F12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12 Key: RKIMETXDACNTIE-UHFFFAOYSA-N;
	SMILES C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)(F)F;
Properties
Chemical formula	C6F12
Molar mass	300.047 g·mol−1
Appearance	clear, waxy solid
Density	1.684 g/cm3
Melting point	52 °C (126 °F; 325 K)[1]
Boiling point	59–60 °C (138–140 °F; 332–333 K)
Solubility	Miscible with organic compounds
Hazards
Main hazards	Irritant
Safety data sheet	MSDS
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Related compounds
Related compounds	Fluorocarbon
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Perfluorocyclohexane or dodecafluorocyclohexane is a chemical which belongs to the class of fluorocarbons, sometimes referred to as perfluorocarbons or PFCs. Fluorocarbons and their derivatives are useful fluoropolymers, refrigerants, solvents, and anesthetics.

Synthesis

Perfluorocyclohexane can be synthesized by fluorination of cyclohexane.[2]

Properties

Perfluorocyclohexane is chemically inert and thermally stable. It is a relatively non-toxic, clear, waxy solid, which has a high vapor pressure and therefore sublimes readily at room temperature. In common with other cyclic perfluorocarbons, perfluoromethylcyclohexane can be detected at extremely low concentrations, making it ideal as a tracer.[3] The molecule predominantly exists in its chair conformation, in which it possesses D_3d molecular symmetry.

References

Sander, M.; Blöchl, W. (January 1965). "Herstellung von Perfluoralkanen und Perfluorcycloalkanen". Chemie Ingenieur Technik - CIT (in German). 37 (1): 7–13. doi:10.1002/cite.330370103.
Sandford G. (2003). "Perfluoroalkanes". Tetrahedron. 59: 437–454. doi:10.1016/s0040-4020(02)01568-5.
Begley P., Foulger B., Simmonds P. (1988). "Femtogram detection of perfluorocarbon tracers using capillary gas chromatography-electron-capture negative ion chemical ionisation mass spectrometry". J. Chromatogr. 445 (1): 119–128. doi:10.1016/s0021-9673(01)84513-1.CS1 maint: uses authors parameter (link)

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[1] Sander, M.; Blöchl, W. (January 1965). "Herstellung von Perfluoralkanen und Perfluorcycloalkanen". Chemie Ingenieur Technik - CIT (in German). 37 (1): 7–13. doi:10.1002/cite.330370103.

[2] Sandford G. (2003). "Perfluoroalkanes". Tetrahedron. 59: 437–454. doi:10.1016/s0040-4020(02)01568-5.

[3] Begley P., Foulger B., Simmonds P. (1988). "Femtogram detection of perfluorocarbon tracers using capillary gas chromatography-electron-capture negative ion chemical ionisation mass spectrometry". J. Chromatogr. 445 (1): 119–128. doi:10.1016/s0021-9673(01)84513-1.CS1 maint: uses authors parameter (link)