Hexafluoro-2-butyne

Hexafluoro-2-butyne
Names
	IUPAC name 1,1,1,4,4,4-Hexafluoro-2-butyne
	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	162.03 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)
Solubility in water	Insoluble
Structure
Dipole moment	0 D
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic gas
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). verify (what is ?) 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

^ 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.