Phenylacetylene

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Phenylacetylene
Phenylacetylene
Phenylacetylene-3D-balls.png
Identifiers
CAS number 536-74-3 YesY
PubChem 10821
ChemSpider 10364 YesY
ChEMBL CHEMBL234833 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H6
Molar mass 102.133 g/mol
Density 0.93 g/cm³
Melting point –45 °C
Boiling point 142-144 °C
Acidity (pKa) 28.8
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Phenylacetylene is an alkyne hydrocarbon containing a 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[edit]

In the laboratory, phenylacetylene can be prepared by elimination of hydrogen bromide from styrene dibromide using sodium amide in ammonia:[1]

Phenylacetylene prepn.png

It can also be prepared by the elimination of hydrogen bromide from bromostyrene using molten potassium hydroxide.[2]

Reactions[edit]

PhCCH trimerisation.svg
AlkyneHydrolysis.svg

See also[edit]

References[edit]

  1. ^ Kenneth N. Campbell and Barbara K. Campbell (1963), "Phenylacetylene", Org. Synth. ; Coll. Vol. 4: 763 
  2. ^ John C. Hessler (1941), "Phenylacetylene", Org. Synth. ; Coll. Vol. 1: 438 
  3. ^ Gerhard Hilt , Thomas Vogler, Wilfried Hess, Fabrizio Galbiati (2005). "A simple cobalt catalyst system for the efficient and regioselective cyclotrimerisation of alkynes". Chemical Communications 2005 (11): 1474–1475. doi:10.1039/b417832g. PMID 15756340.