Diphenylacetylene

• Tolan
• Diphenylacetylene
• 2- Phenylethinylbenzen (IUPAC)

White needles

0.99 g · cm -3 ( 25 ° C)

59-61 ° C

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Diphenylethyne is the chemical compound C6H5C ≡ CC6H5. The molecule consists of two phenyl groups, which are bound to both ends of a alkinischen triple bond. The connection can be regarded both as ethyne derivative as a benzene derivative.

Diphenylethyne is a colorless crystalline solid, which is often used as a basic building block in organic synthesis and as a ligand in organometallic chemistry.

Production

Diphenylethyne can be prepared in several ways:

• Condensation of benzil with hydrazine yields the hydrazone, which is then oxidized to mercury (II ) oxide.
• Bromination of stilbene ( diphenylethene ) and subsequent dehydrohalogenation. However, the product may be contaminated with heavy detachable stilbene.
• Stephens - Castro coupling of iodobenzene with the copper salt of Phenylethins.

Significant derivatives

• The reaction with tetraphenylcyclopentadienone provides hexaphenylbenzene.
• The reaction with benzal chloride in the presence of potassium tert- butoxide provides the 3- Alkoxycyclopropen which converts into hydrogen bromide to Triphenylcyclopropeniumbromid.