|Jmol-3D images||Image 1|
|Molar mass||178.24 g/mol|
|Density||0.990 g cm-3, solid|
62.5 °C, 335.7 K, 144.5 °F
0–97 °C/0.3 mmHg
|Solubility in water||insoluble|
|Molecular shape||sp2 and sp at carbon|
|Dipole moment||0 D|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 and as a ligand in organometallic chemistry.
Several preparations for this compound exist:
- 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
- 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", Org. Synth.; Coll. Vol. 4: 377
- Lee Irvin Smith and M. M. Falkof, "Diphenylacetylene", Org. Synth.; Coll. Vol. 3: 350
- Fieser, L. F., "Hexaphenylbenzene", Org. Synth.; Coll. Vol. 5: 604
- Xu, R. Breslow, R., "1,2,3-Triphenylcyclopropendium Bromide", Org. Synth.; Coll. Vol. 9: 730