Hexafluorocyclobutene is the
organofluorine compound
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refri ...
with the formula (CF
2)
2(CF)
2. A colorless gas, it is a precursor to a variety of compounds, including
squaric acid
Squaric acid, also called quadratic acid because its four carbon atoms approximately form a square, is a diprotic organic acid with the chemical formula C4O2(OH)2.
The conjugate base of squaric acid is the hydrogensquarate anion ; and the conjug ...
. Hexafluorocyclobutene is prepared in two steps from
chlorotrifluoroethylene
Chlorotrifluoroethylene (CTFE) is a chlorofluorocarbon with chemical formula CFCl=CF2. It is commonly used as a refrigerant in cryogenic applications. CTFE has a carbon-carbon double bond and so can be polymerized to form polychlorotrifluoroethyl ...
. The thermal dimerization gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane. Dechlorination of the latter gives hexafluorocyclobutene:
:C
4F
6Cl
2 + Zn -> C
4F
6 + ZnCl
2
Safety
Reminiscent of
perfluoroisobutene
Perfluoroisobutene (PFIB) is the perfluorocarbon counterpart of the hydrocarbon isobutene and has the formula (CF3)2C=CF2. An alkene, it is a colorless gas that is notable as a highly toxic perfluoroalkene. Few simple alkenes are as toxic.
Safet ...
, hexafluorocyclobutene is quite toxic with an LD = 6000 mg/min/m
−3 (mice).
[{{cite book , doi=10.1016/B978-008043405-6/50040-2, chapter=Highly-toxic fluorine compounds, title=Fluorine Chemistry at the Millennium, year=2000, last1=Timperley, first1=Christopher M., pages=499–538, isbn=9780080434056]
See also
*
Hexafluoro-2-butyne
Hexafluoro-2-butyne (HFB) is a fluorocarbon with the chemical structure CF3C≡CCF3. HFB is a particularly electrophilic acetylene derivative, and hence a potent dienophile for Diels–Alder reactions.
HFB is prepared by the action of sulfur te ...
*
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.
It can be prepared by coupling of C2 compound ...
References
Perfluorinated compounds
Cycloalkenes