Diphenylacetylene

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.

Diphenylacetylene
Names
Preferred IUPAC name
1,1'-(Ethyne-1,2-diyl)dibenzene
Other names
1,2-Diphenylethyne
2-Phenylethynylbenzene
Tolan
Diphenylacetylene
Identifiers
3D model (JSmol)
606478
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.206
EC Number
  • 207-926-6
UNII
Properties
C14H10
Molar mass 178.234 g·mol−1
Appearance Colorless solid
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
Insoluble
Structure
0 D
Hazards
Safety data sheet Oxford MSDS
Related compounds
Related compounds
 2-Butyne
Dimethyl acetylenedicarboxylate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

In one preparation for this compound, benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury oxide.[1] Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation,[2] Yet another method starts involves the coupling iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling.

Derivatives

Reaction of Ph2C2 with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene.[3] Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.[4]

References
  1. Cope, A. C.; Smith, D. S.; Cotter, R. J. "Diphenylacetylene". Organic Syntheses.; Collective Volume, 4, p. 377
  2. Lee Irvin Smith and M. M. Falkof. "Diphenylacetylene". Organic Syntheses.; Collective Volume, 3, p. 350
  3. Fieser, L. F. "Hexaphenylbenzene". Organic Syntheses.; Collective Volume, 5, p. 604
  4. 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
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