Girish Mahajan (Editor)

Diphenylacetylene

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Formula
  
C14H10

Melting point
  
62.5 °C

Appearance
  
colorless solid

Molar mass
  
178.24 g/mol

Density
  
990 kg/m³


Related compounds
  
C2Me2 Dimethylacetylenedicarboxylate

Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of phenyl groups attached to both ends of an alkyne. It is a colorless crystalline material that is widely used as a building block in organic synthesis and as a ligand in organometallic chemistry.

Contents

Diphenylacetylene Diphenylacetylene50165513CNMR

Preparation

Several preparations for this compound exist:

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  • benzil is condensed with hydrazine to give the bis (hydrazone), which is oxidized with mercury oxide.
  • stilbene is brominated, then dehydrohalogenated, but the product can be contaminated with stilbene, which is difficult to remove.
  • One method starts from iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling

    • Interesting derivatives

    Diphenylacetylene Diphenylacetylene 98 SigmaAldrich

  • Reaction of Ph2C2 with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene.
  • Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.

    • Diphenylacetylene Diphenylacetylene Wikipedia

    Diphenylacetylene CV3P0350gif

    References

    Diphenylacetylene Wikipedia
    (Text) CC BY-SA