Diphenylacetylene

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Diphenylacetylene
DiphenylacetyleneSVG.svg
Diphenylacetylene-3D-balls.png
Diphenylacetylene-3D-vdW.png
Names
Preferred IUPAC name
1,1′-Ethynediyldibenzene
Other names
Tolane
1,2-Diphenylethyne
2-Phenylethynylbenzene
Tolan
Diphenylacetylene
Identifiers
  • 501-65-5 checkY
3D model (JSmol)
606478
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.206 Edit this at Wikidata
EC Number
  • 207-926-6
UNII
  • InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H checkY
    Key: JRXXLCKWQFKACW-UHFFFAOYSA-N checkY
  • InChI=1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
    Key: JRXXLCKWQFKACW-UHFFFAOYAN
  • c1ccc(cc1)C#Cc2ccccc2
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
Dipole moment
 0 D
Hazards
Safety data sheet (SDS) Oxford 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 [77 °F], 100 kPa).
checkY  (what is checkY☒N ?)
Infobox references

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.[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. ^ a b 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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