|Molar mass||178.24 g/mol|
|Density||0.990 g cm−3, solid|
|Melting point||62.5 °C (144.5 °F; 335.6 K)|
|Boiling point||170 °C (338 °F; 443 K) at 19 mmHg|
|sp2 and sp at carbon|
|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: / ?)(|
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.
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, p. 377
- Lee Irvin Smith and M. M. Falkof. "Diphenylacetylene". Org. Synth.; Coll. Vol. 3, p. 350
- Fieser, L. F. "Hexaphenylbenzene". Org. Synth.; Coll. Vol. 5, p. 604
- Xu, R. Breslow, R. "1,2,3-Triphenylcyclopropendium Bromide". Org. Synth.; Coll. Vol. 9, p. 730