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Diphenylacetylene

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(Redirected from Tolane)
Diphenylacetylene
Names
Preferred IUPAC name 1,1′-Ethynediyldibenzene
Other names Tolane
1,2-Diphenylethyne
Diphenylethyne
2-Phenylethynylbenzene
Tolan
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 606478
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.206 Edit this at Wikidata
EC Number
  • 207-926-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10HKey: JRXXLCKWQFKACW-UHFFFAOYSA-N
  • InChI=1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10HKey: JRXXLCKWQFKACW-UHFFFAOYAN
SMILES
  • c1ccc(cc1)C#Cc2ccccc2
Properties
Chemical formula C14H10
Molar mass 178.234 g·mol
Appearance Colorless solid
Density 1.136 g cm
Melting point 62.5 °C (144.5 °F; 335.6 K)
Boiling point 170 °C (338 °F; 443 K) at 19 mmHg
Solubility in water Insoluble
Structure
Dipole moment 0 D
Hazards
Safety data sheet (SDS) Fisher Scientific MSDS
Related compounds
Related compounds But-2-yne
Dimethyl acetylenedicarboxylate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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. Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation. Yet another method involves the coupling of iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene.

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

Derivatives

Reaction of diphenylacetylene with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene in a Diels–Alder reaction.

Dicobalt octacarbonyl catalyzes alkyne trimerisation of diphenylacetylene to form hexaphenylbenzene.

Diphenylacetylene cyclotrimerization using dicobalt octacarbonyl

Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords 3-tert-butoxy-1,2,3-triphenylcyclopropene, which converts to 1,2,3-triphenylcyclopropenium bromide after the elimination of tert-butoxide.

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". Organic Syntheses. 34: 42. doi:10.15227/orgsyn.034.0042.
  3. Lee Irvin Smith; M. M. Falkof (1942). "Diphenylacetylene". Organic Syntheses. 22: 50. doi:10.15227/orgsyn.022.0050.
  4. Fieser, L. F. (1966). "Hexaphenylbenzene". Organic Syntheses. 46: 44. doi:10.15227/orgsyn.046.0044.
  5. Vij, V.; Bhalla, V.; Kumar, M. (8 August 2016). "Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold". Chemical Reviews. 116 (16): 9565–9627. doi:10.1021/acs.chemrev.6b00144.
  6. Xu, Ruo; Breslow, Ronald (1997). "1,2,3-Triphenylcyclopropenium Bromide". Organic Syntheses. 74: 72. doi:10.15227/orgsyn.074.0072.
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