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 978-3-527-30673-2.
  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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