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Hexafluoro-2-butyne

Hexafluoro-2-butyne


IUPAC name	1,1,1,4,4,4-Hexafluoro-2-butyne
Other names	HFB
Identifiers
CAS number	692-50-2
RTECS number	ES0702500
SMILES	FC(F)(F)C#CC(F)(F)F
Properties
Molecular formula	C₄F₆
Molar mass	162.03 g/mol
Appearance	Colorless gas
Density	1.602 g/cm³
Melting point	-117 °C
Boiling point	-25 °C
Solubility in water	Insoluble
Structure
Dipole moment	0 D
Hazards
Main hazards	Toxic gas
R-phrases	12-23
S-phrases	16-33-45
Related Compounds
Related compounds	Dimethyl acetylenedicarboxylate, hexachlorobutadiene, acetylene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.^[1]^[2]

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

References

^ 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.
^ E S Turbanova, A A Petrov (1991). "Perfluoroalkyl(aryl)acetylenes". Russian Chemical Reviews 60 (5): 501-523. doi:10.1070/RC1991v060n05ABEH001092.