Hexafluoro-2-butyne

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
CAS Number
  • 692-50-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 62855 checkY
ECHA InfoCard 100.010.667 Edit this at Wikidata
EC Number
  • 211-732-7
PubChem CID
  • 69654
RTECS number
  • ES0702500
CompTox Dashboard (EPA)
  • DTXSID3061003 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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)
Solubility in water
 Insoluble
Structure
Dipole moment
 0 D
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic gas
GHS labelling:
Pictograms
 GHS04: Compressed GasGHS06: Toxic
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).
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Infobox references
Chemical compound

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]

Synthesis and reactions

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

It reacts with sulfur to give 3,4-bis(trifluoromethyl)-1,2-dithiete.

Cycloaddition of HFB and dithionitronium (NS2+) gives the 1,2,5-dithiazolium cation. This derivative can be reduced to the 7 electron neutral radical. This particular 1,3,5-dithiazole is also rare example of a radical that can be obtained as solid, liquid, and gaseous states. As a gas, it is blue.[4]

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.
  4. ^ Brownridge, Scott; Du, Hongbin; Fairhurst, Shirley A.; Haddon, Robert C.; Oberhammer, Heinz; Parsons, Simon; Passmore, Jack; Schriver, Melbourne J.; Sutcliffe, Leslie H.; Westwood, Nicholas P. C. (2000). "The Isolation, Characterisation, Gas Phase Electron Diffraction and Crystal Structure of the Thermally Stable Radical CF3CSNSCCF3". Journal of the Chemical Society, Dalton Transactions (19): 3365–3382. doi:10.1039/B001489N.