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Phenylacetylene

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Density
  
930 kg/m³

Molar mass
  
102.133 g/mol

Formula
  
C8H6

Phenylacetylene FilePhenylacetylene3svg Wikimedia Commons

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.

Contents

Phenylacetylene Phenylacetylene CAS 536743 807044

Synthesis of phenylacetylene 2 method


Preparation

Phenylacetylene Phenylacetylene

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

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

Reactions

Phenylacetylene httpsuploadwikimediaorgwikipediacommonsthu

  • Phenylacetylene can be reduced (hydrogenated) by hydrogen over Lindlar catalyst to give styrene.
  • It undergoes a metal catalyzed trimerization to give 1,2,4- (97%) and 1,3,5-triphenylbenzene:
    • Phenylacetylene Phenylacetylene 98 SigmaAldrich

  • Choosing a rhodium catalyst leads to the cyclotrimerization producing both the 1,2,4- and 1,3,5- isomers along with substantial quantities of acyclic enyne dimer products:
  • It undergoes a hydration reaction, catalyzed by gold(III) or mercury(II), to give acetophenone.

    • Phenylacetylene Phenyl acetylene113C 99 atom 13C SigmaAldrich

    Phenylacetylene Phenylacetylene C8H6 ChemSpider

    Phenylacetylene Phenylacetylene CAS Number 536743

    References

    Phenylacetylene Wikipedia
    (Text) CC BY-SA


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