Hexafluorocyclobutene

Hexafluorocyclobutene
Names
	Other names 1,2,3,3,4,4-hexafluorocyclobutene, perfluorocyclobutene
Identifiers
CAS Number	697-11-0;
3D model (JSmol)	Interactive image;
ChemSpider	12242;
EC Number	211-803-2;
PubChem CID	12767;
CompTox Dashboard (EPA)	DTXSID2073229;
	InChI InChI=1S/C4F6/c5-1-2(6)4(9,10)3(1,7)8 Key: QVHWOZCZUNPZPW-UHFFFAOYSA-N;
	SMILES C1(=C(C(C1(F)F)(F)F)F)F;
Properties
Chemical formula	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

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] Dichlorination of the latter gives hexafluorocyclobutene:[3]

C₄F₆Cl₂ + Zn C₄F₆ + ZnCl₂

Safety

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

References

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.
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.
Fuller, G.; Tatlow, J. C. (1961). "Some Isomeric Hexafluorocyclobutanes and Pentafluorocyclobutenes". Journal of the Chemical Society (Resumed): 3198. doi:10.1039/JR9610003198.
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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[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.

Hexafluorocyclobutene

See also

Safety

References