Hexafluorocyclobutene

Hexafluorocyclobutene is the organofluorine compound with the formula (CF2)2(CF)2. A colorless gas, it is a precursor to a variety of compounds, including squaric acid.[1] Hexafluorocyclobutene is prepared in two steps from chlorotrifluoroethylene. The thermal dimerization gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane.[2] Dechlorination of the latter gives hexafluorocyclobutene:[3]

C4F6Cl2 + Zn -> C4F6 + ZnCl2
Hexafluorocyclobutene
Names
Preferred IUPAC name
1,2,3,3,4,4-Hexafluorocyclobut-1-ene
Other names
1,2,3,3,4,4-hexafluorocyclobutene, perfluorocyclobutene
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 211-803-2
UNII
  • InChI=1S/C4F6/c5-1-2(6)4(9,10)3(1,7)8
    Key: QVHWOZCZUNPZPW-UHFFFAOYSA-N
  • C1(=C(C(C1(F)F)(F)F)F)F
Properties
C4F6
Molar mass 162.034 g·mol−1
Appearance colorless gas
Melting point −60 °C (−76 °F; 213 K)
Boiling point 5.5 °C (41.9 °F; 278.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Safety

Reminiscent of perfluoroisobutene, hexafluorocyclobutene is quite toxic with an LD = 6000 mg/min/m−3 (mice).[4]

See also

References
  1. David M. Lemal, Xudong Chen (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.
  2. Buxton, M. W.; Ingram, D. W.; Smith, F.; Stacey, M.; Tatlow, J. C. (1952). "The High-Temperature Dimerisation of Chlorotrifluoroethylene". Journal of the Chemical Society (Resumed): 3830. doi:10.1039/JR9520003830.
  3. Fuller, G.; Tatlow, J. C. (1961). "Some Isomeric Hexafluorocyclobutanes and Pentafluorocyclobutenes". Journal of the Chemical Society (Resumed): 3198. doi:10.1039/JR9610003198.
  4. Timperley, Christopher M. (2000). "Highly-toxic fluorine compounds". Fluorine Chemistry at the Millennium. pp. 499–538. doi:10.1016/B978-008043405-6/50040-2. ISBN 9780080434056.
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