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Hexafluorobutadiene

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(Redirected from 1,1,2,3,4,4-Hexafluoro-1,3-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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.620 Edit this at Wikidata
EC Number
  • 211-681-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4F6/c5-1(3(7)8)2(6)4(9)10Key: LGPPATCNSOSOQH-UHFFFAOYSA-N
SMILES
  • C(=C(F)F)(C(=C(F)F)F)F
Properties
Chemical formula C4F6
Molar mass 162.034 g·mol
Appearance colorless gas
Density 1.44 g/cm (@15 °C)
Melting point −132 °C (−206 °F; 141 K)
Boiling point 6 °C (43 °F; 279 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS06: Toxic
Signal word Danger
Hazard statements H220, H331
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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 dechlorination of 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane.

Hexafluorobutadiene dimerizes via a process at 150 °C to give perfluorinated divinylcyclobutanes.

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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