Diphenylacetylene

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Diphenylacetylene
DiphenylacetyleneSVG.svg
Diphenylacetylene-3D-balls.png
Diphenylacetylene-3D-vdW.png
Names
IUPAC name
2-phenylethynylbenzene
Other names
Tolan
Diphenylacetylene
1,2-diphenylethyne
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.206
Properties
C14H10
Molar mass 178.24 g/mol
Appearance colorless solid
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
insoluble
Structure
sp2 and sp at carbon
0 D
Hazards
Safety data sheet Oxford MSDS
Related compounds
Related compounds
C2Me2
Dimethylacetylenedicarboxylate
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

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.

Preparation[edit]

Several preparations for this compound exist:

Interesting derivatives[edit]

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

Drugs[edit]

  1. Rxn with methyl 3-benzyl-sydnone-4-acetate gives Isofezolac (Sofenac).
  2. Bufezolac
  3. Broparestrol, Etacstil.
  4. Diphenidine, then presumably lefetamine etc also.

References[edit]

  1. ^ a b Cope, A. C.; Smith, D. S.; Cotter, R. J. "Diphenylacetylene". Org. Synth. ; Coll. Vol., 4, p. 377 
  2. ^ Lee Irvin Smith and M. M. Falkof. "Diphenylacetylene". Org. Synth. ; Coll. Vol., 3, p. 350 
  3. ^ Fieser, L. F. "Hexaphenylbenzene". Org. Synth. ; Coll. Vol., 5, p. 604 
  4. ^ Xu, R. Breslow, R. "1,2,3-Triphenylcyclopropendium Bromide". Org. Synth.  ; Coll. Vol., 9, p. 730