Diphenylacetylene

Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is 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
Tolane
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 1.136 g cm−3[1]
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 and structure

In one preparation for this compound, benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury(II) oxide.[2] Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation,[3] Yet another method starts involves the coupling iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling.

Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers.[1]

Derivatives

Reaction of diphenylacetylene with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene.[4] Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which converts to the cyclopropenium ion.[5]

References
  1. Mavridis, A.; Moustakali-Mavridis, I. (1977). "A Reinvestigation of Tolane". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 33 (11): 3612–3615. doi:10.1107/S0567740877011674.
  2. Cope, A. C.; Smith, D. S.; Cotter, R. J. (1954). "Diphenylacetylene". 34: 42. doi:10.15227/orgsyn.034.00424. Cite journal requires |journal= (help)
  3. Lee Irvin Smith; M. M. Falkof (1942). "Diphenylacetylene". 22: 50. doi:10.15227/orgsyn.022.0050. Cite journal requires |journal= (help)
  4. Fieser, L. F. (1966). "Hexaphenylbenzene". 46: 44. doi:10.15227/orgsyn.046.0044. Cite journal requires |journal= (help)
  5. Xu, Ruo; Breslow, Ronald (1997). "1,2,3-Triphenylcyclopropendium Bromide". 74: 72. doi:10.15227/orgsyn.074.0072. Cite journal requires |journal= (help)
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