Hexafluoroisobutylene

Hexafluoroisobutylene
Names
	Preferred IUPAC name 3,3,3-Trifluoro-2-(trifluoromethyl)prop-1-ene
	Other names hexafluoroisobutene
Identifiers
CAS Number	382-10-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	82578;
ECHA InfoCard	100.006.219
EC Number	206-840-6;
PubChem CID	91450;
UNII	P9GQF23ZL8 ;
CompTox Dashboard (EPA)	DTXSID9052056 ;
	InChI InChI=1S/C4H2F6/c1-2(3(5,6)7)4(8,9)10/h1H2 Key: QMIWYOZFFSLIAK-UHFFFAOYSA-N;
	SMILES C=C(C(F)(F)F)C(F)(F)F;
Properties
Chemical formula	C4H2F6
Molar mass	164.050 g·mol−1
Appearance	colorless gas
Boiling point	14.1 °C (57.4 °F; 287.2 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H331, H341, H372
Precautionary statements	P201, P202, P260, P261, P264, P270, P271, P281, P304+P340, P308+P313, P311, P314, P321, P403+P233, P405, P410+P403, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hexafluoroisobutylene is an organofluorine compound with the formula (CF₃)₂C=CH₂. This colorless gas is structurally similar to isobutylene. It is used as a comonomer in the production of modified polyvinylidene fluoride. It is produced in a multistep process starting with the reaction of acetic anhydride with hexafluoroacetone.^[1] It is oxidized by sodium hypochlorite to hexafluoroisobutylene oxide. As expected, it is a potent dienophile.^[2]

References

^ Günter Siegemund; Werner Schwertfeger; Andrew Feiring; Bruce Smart; Fred Behr; Herward Vogel; Blaine McKusick; Peer Kirsch (2016). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–56. doi:10.1002/14356007.a11_349.pub2. ISBN 978-3-527-30673-2.
^ Murphy, Peter M. (2013). "The chemistry and utility of hexafluoroisobutylene (HFIB) and hexafluoroisobutylene oxide (HFIBO)". Journal of Fluorine Chemistry. 156: 345–362. doi:10.1016/j.jfluchem.2013.07.015.