Hexafluoroisobutylene

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]

Hexafluoroisobutylene
Names
Preferred IUPAC name
3,3,3-Trifluoro-2-(trifluoromethyl)prop-1-ene
Other names
hexafluoroisobutene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.219
EC Number
  • 206-840-6
UNII
  • InChI=1S/C4H2F6/c1-2(3(5,6)7)4(8,9)10/h1H2
    Key: QMIWYOZFFSLIAK-UHFFFAOYSA-N
  • C=C(C(F)(F)F)C(F)(F)F
Properties
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:
GHS04: Compressed GasGHS06: ToxicGHS08: Health hazard
Danger
H280, H331, H341, H372
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

See also

References
  1. 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 9783527306732.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  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.
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