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
Preferred IUPAC name
1,1,1,4,4,4-Hexafluorobut-2-yne
Other names
HFB
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.667 Edit this at Wikidata
EC Number
  • 211-732-7
RTECS number
  • ES0702500
  • InChI=1S/C4F6/c5-3(6,7)1-2-4(8,9)10 checkY
    Key: WBCLXFIDEDJGCC-UHFFFAOYSA-N checkY
  • InChI=1/C4F6/c5-3(6,7)1-2-4(8,9)10
    Key: WBCLXFIDEDJGCC-UHFFFAOYAY
  • FC(F)(F)C#CC(F)(F)F
Properties
C4F6
Molar mass 162.034 g·mol−1
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
Dipole moment
 0 D
Hazards[1]
Main hazards Toxic gas
GHS labelling:
GHS04: Compressed GasGHS06: Toxic
Signal word
 Danger
H280, H331
P261, P311, P410+P403
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).
☒N  (what is checkY☒N ?)
Infobox references

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.[2][3]

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

References[]

  1. ^ "Hexafluoro-2-butyne 99%". Sigma-Aldrich.
  2. ^ Essers, Michael; Haufe, Günter (2006). "Hexafluoro-2-butyne". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00669. ISBN 0471936235.
  3. ^ 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.
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