Diphenylacetylene

Diphenylacetylene
IUPAC name 2-phenylethynylbenzene
Other names Tolan Diphenylacetylene 1,2-diphenylethyne
Identifiers
CAS number	501-65-5 Y
PubChem	10390
ChemSpider	9961 Y
ChEBI	CHEBI:51579 Y
ChEMBL	CHEMBL223309 Y
Jmol-3D images	Image 1
SMILES c1ccc(cc1)C#Cc2ccccc2
InChI InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H Y Key: JRXXLCKWQFKACW-UHFFFAOYSA-N Y InChI=1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H Key: JRXXLCKWQFKACW-UHFFFAOYAN
Properties
Molecular formula	C14H10
Molar mass	178.24 g/mol
Appearance	colorless solid
Density	0.990 g cm-3, solid
Melting point	62.5 °C, 335.7 K, 144.5 °F
Boiling point	0–97 °C/0.3 mmHg
Solubility in water	insoluble
Structure
Molecular shape	sp2 and sp at carbon
Dipole moment	0 D
Hazards
MSDS	Oxford MSDS
Related compounds
Related compounds	C2Me2 Dimethylacetylenedicarboxylate
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 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. ↑ 1.0 1.1 Cope, A. C.; Smith, D. S.; Cotter, R. J., "Diphenylacetylene", Org. Synth. ; Coll. Vol. 4: 377 
2. ↑ Lee Irvin Smith and M. M. Falkof, "Diphenylacetylene", Org. Synth. ; Coll. Vol. 3: 350 
3. ↑ Fieser, L. F., "Hexaphenylbenzene", Org. Synth. ; Coll. Vol. 5: 604 
4. ↑ Xu, R. Breslow, R., "1,2,3-Triphenylcyclopropendium Bromide", Org. Synth. ; Coll. Vol. 9: 730