Phenylacetylene

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Phenylacetylene
Phenylacetylene
Names
Preferred IUPAC name
Ethynylbenzene
Other names
Phenylacetylene
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.007.861 Edit this at Wikidata
UNII
  • InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H checkY
    Key: UEXCJVNBTNXOEH-UHFFFAOYSA-N checkY
  • InChI=1/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
    Key: UEXCJVNBTNXOEH-UHFFFAOYAC
  • C#Cc1ccccc1
Properties
C8H6
Molar mass 102.133 g/mol
Density 0.93 g/cm3
Melting point −45 °C (−49 °F; 228 K)
Boiling point 142 to 144 °C (288 to 291 °F; 415 to 417 K)
Acidity (pKa) 28.7 (DMSO),[1]
23.2 (aq, extrapolated)[2]
-72.01·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Phenylacetylene is an

phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene
; being a liquid, it is easier to handle than acetylene gas.

Preparation

In the laboratory, phenylacetylene can be prepared by elimination of hydrogen bromide from styrene dibromide using sodium amide in ammonia:[3]

It can also be prepared by the elimination of hydrogen bromide from bromostyrene using molten

TBAF.[5]

Reactions

Phenylacetylene is a prototypical terminal acetylene, undergoing many reactions expected of that functional group. It undergoes semi

trimerization, and even polymerization.[7][8]

In the presence of gold or mercury reagents, phenylacetylene hydrates to give acetophenone:

PhC2H + H2O → PhC(O)CH3

See also

References

  1. doi:10.1021/ar00156a004
    .
  2. doi:10.1021/ja00736a045
    .
  3. doi:10.15227/orgsyn.030.0072
    .
  4. doi:10.15227/orgsyn.002.0067
    .
  5. ISBN 978-0471936237
    .
  6. doi:10.15227/orgsyn.045.0039
    .
  7. PMID 15756340
    .
  8. doi:10.1016/S1381-1169(03)00315-7
    .
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