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.[1][2]

Hexafluoro-2-butyne

Names
IUPAC name 1,1,1,4,4,4-hexafluorobut-2-yne
Other names HFB
Identifiers
CAS Number	692-50-2
3D model (JSmol)	Interactive image
ChemSpider	62855
ECHA InfoCard	100.010.667
PubChem CID	69654
RTECS number	ES0702500
CompTox Dashboard (EPA)	DTXSID3061003
InChI InChI=1S/C4F6/c5-3(6,7)1-2-4(8,9)10 Key: WBCLXFIDEDJGCC-UHFFFAOYSA-N InChI=1/C4F6/c5-3(6,7)1-2-4(8,9)10 Key: WBCLXFIDEDJGCC-UHFFFAOYAY
SMILES FC(F)(F)C#CC(F)(F)F
Properties
Chemical formula	C4F6
Molar mass	162.034 g·mol^−1
Appearance	Colorless gas
Density	1.602 g/cm^3
Melting point	−117 °C (−179 °F; 156 K)
Boiling point	−25 °C (−13 °F; 248 K)
Solubility in water	Insoluble
Structure
Dipole moment	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R-phrases (outdated)	R12 R23
S-phrases (outdated)	S16 S33 S45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

HFB is prepared by the action of sulfur tetrafluoride on acetylenedicarboxylic acid or by the reaction of potassium fluoride (KF) with hexachlorobutadiene.

References

1. Essers, Michael; Haufe, Günter (2006). "Hexafluoro-2-butyne". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00669. ISBN 0471936235.
2. E S Turbanova, A A Petrov (1991). "Perfluoroalkyl(aryl)acetylenes". Russian Chemical Reviews. 60 (5): 501–523. Bibcode:1991RuCRv..60..501T. doi:10.1070/RC1991v060n05ABEH001092.