Hexafluoro-2-butyne

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Hexafluoro-2-butyne
Skeletal formula of hexafluoro-2-butyne
Ball-and-stick model of hexafluorobut-2-yne
Names
IUPAC name
1,1,1,4,4,4-Hexafluoro-2-butyne
Other names
HFB
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.667
RTECS number ES0702500
Properties
C4F6
Molar mass 162.03 g/mol
Appearance Colorless gas
Density 1.602 g/cm3
Melting point −117 °C (−179 °F; 156 K)
Boiling point −25 °C (−13 °F; 248 K)
Insoluble
Structure
0 D
Hazards
Main hazards Toxic gas
R-phrases (outdated) R12 R23
S-phrases (outdated) S16 S33 S45
Related compounds
Related compounds
Dimethyl acetylenedicarboxylate
Hexachlorobutadiene
Acetylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hexafluoro-2-butyne is the fluorocarbon with the formula CF3C≡CCF3. HFB, as it is known also, is a particularly electrophilic acetylene, hence a potent dienophile for Diels–Alder reactions.[1][2]

It is prepared by the action of sulfur tetrafluoride on acetylenedicarboxylic acid and the reaction of KF with hexachlorobutadiene.

References[edit]

  1. ^ Essers, M.; Haufe, G. "Hexafluoro-2-butyne” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
  2. ^ E S Turbanova, A A Petrov (1991). "Perfluoroalkyl(aryl)acetylenes". Russian Chemical Reviews. 60 (5): 501–523. doi:10.1070/RC1991v060n05ABEH001092.