Hexafluorobutadiene

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Hexafluorobutadiene
Hexafluorobutadiene.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-681-0
PubChem CID
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
Appearancecolorless 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:
GHS-pictogram-flamme.svg GHS-pictogram-bottle.svg GHS-pictogram-skull.svg
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).

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.

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.[ citation needed ]

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

See also

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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.