Hexafluorobutadiene

Hexafluorobutadiene is an organofluorine compound with the formula (CF2=CF)2. A colorless gas, it has attracted attention as an etchant in microelectronics. It is the perfluoroanalogue of butadiene.

Hexafluorobutadiene
Names
Preferred IUPAC name
Hexafluorobuta-1,3-diene
Other names
1,1,2,3,4,4-Hexafluoro-1,3-butadiene, FC 2316
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.620
EC Number
  • 211-681-0
UNII
  • InChI=1S/C4F6/c5-1(3(7)8)2(6)4(9)10
    Key: LGPPATCNSOSOQH-UHFFFAOYSA-N
  • C(=C(F)F)(C(=C(F)F)F)F
Properties
C4F6
Molar mass 162.034 g·mol−1
Appearance colorless gas
Density 1.44 g/cm3 (@15 °C)
Melting point −132 °C (−206 °F; 141 K)
Boiling point 6 °C (43 °F; 279 K)
Hazards
GHS labelling:
GHS02: FlammableGHS04: Compressed GasGHS06: Toxic
Danger
H220, H280, H331
P210, P261, P271, P304+P340, P311, P321, P377, P381, P403, 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

It can be prepared by coupling of C2 compounds such as from chlorotrifluoroethylene or bromotrifluoroethylene. Routes from C4 species have also been demonstrated. For example, an early synthesis involved Zn-induced dechlorinaion of 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane.

Hexafluorobutadiene dimerizes via a [2+2] process at 150 °C to give perfluorinated divinylcyclobutanes.[1]

See also

References
  1. Lemal, David M.; Chen, Xudong (2005). "Fluorinated Cyclobutanes and Their Derivatives". In Zvi Rappoport; Joel F. Liebman (eds.). The Chemistry of Cyclobutanes. PATAI'S Chemistry of Functional Groups. pp. 955–1029. doi:10.1002/0470864028.ch21. ISBN 0470864001.
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