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.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||178.234 g·mol−1|
|Density||0.990 g cm−3|
|Melting point||62.5 °C (144.5 °F; 335.6 K)|
|Boiling point||170 °C (338 °F; 443 K) at 19 mmHg|
|Safety data sheet||Oxford MSDS|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
In one preparation for this compound, benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury oxide. Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation, Yet another method starts involves the coupling iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling.
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.
- Cope, A. C.; Smith, D. S.; Cotter, R. J. "Diphenylacetylene". Organic Syntheses.; Collective Volume, 4, p. 377
- Lee Irvin Smith and M. M. Falkof. "Diphenylacetylene". Organic Syntheses.; Collective Volume, 3, p. 350
- Fieser, L. F. "Hexaphenylbenzene". Organic Syntheses.; Collective Volume, 5, p. 604
- Xu, Ruo; Breslow, Ronald (1997). "1,2,3-Triphenylcyclopropendium Bromide". Organic Syntheses. 74: 72. doi:10.15227/orgsyn.074.0072.; Collective Volume, 9, p. 730