Diphenylacetylene

Diphenylacetylene

Names
IUPAC name 2-phenylethynylbenzene
Other names Tolan Diphenylacetylene 1,2-diphenylethyne
Identifiers
CAS Number	501-65-5
ChEBI	CHEBI:51579
ChEMBL	ChEMBL223309
ChemSpider	9961
Jmol interactive 3D	Image
PubChem	10390
InChI InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H Key: JRXXLCKWQFKACW-UHFFFAOYSA-N InChI=1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H Key: JRXXLCKWQFKACW-UHFFFAOYAN
SMILES c1ccc(cc1)C#Cc2ccccc2
Properties
Chemical formula	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
Solubility in water	insoluble
Structure
Molecular shape	sp2 and sp at carbon
Dipole moment	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

Several preparations for this compound exist:

• benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury oxide.^[1]
• stilbene is brominated, then dehydrohalogenated,^[2] but the product can be contaminated with stilbene, which is difficult to remove.^[1]
• One method starts from iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling

Interesting 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". 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