Hexafluoro-2-butyne

Chembox new
Name = Hexafluoro-2-butyne
ImageFile = Hexafluorobutyne.png ImageName = Skeletal formula of hexafluoro-2-butyne
ImageFile1 = Hexafluorobut-2-yne-3D-balls.png ImageName1 = Ball-and-stick model of hexafluorobut-2-yne
IUPACName = 1,1,1,4,4,4-Hexafluoro-2-butyne
OtherNames = HFB
Section1 = Chembox Identifiers
SMILES = FC(F)(F)C#CC(F)(F)F
CASNo = 692-50-2
RTECS = ES0702500
Section2 = Chembox Properties
Formula = C₄F₆
MolarMass = 162.03 g/mol
Appearance = Colorless gas
Density = 1.602 g/cm³
Solubility = Insoluble
MeltingPt = -117 °C
BoilingPt = -25 °C
Section3 = Chembox Structure
Dipole = 0 D
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = Toxic gas
FlashPt =
RPhrases = 12-23
SPhrases = 16-33-45
Section8 = Chembox Related
OtherCpds = Dimethyl acetylenedicarboxylate,
hexachlorobutadiene,
acetylene

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. [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.] [cite journal
title = Perfluoroalkyl(aryl)acetylenes
author = E S Turbanova, A A Petrov
journal = Russian Chemical Reviews
year = 1991
volume = 60
issue = 5
pages = 501–523
doi = 10.1070/RC1991v060n05ABEH001092]

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

References