Diphenylacetylene

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.

Diphenylacetylene

Names
Preferred IUPAC name 1,1'-(Ethyne-1,2-diyl)dibenzene
Other names Tolane 1,2-Diphenylethyne 2-Phenylethynylbenzene Tolan Diphenylacetylene
Identifiers
CAS Number	501-65-5
3D model (JSmol)	Interactive image
Beilstein Reference	606478
ChEBI	CHEBI:51579
ChEMBL	ChEMBL223309
ChemSpider	9961
ECHA InfoCard	100.007.206
EC Number	207-926-6
PubChem CID	10390
UNII	Y70JA8HB75
CompTox Dashboard (EPA)	DTXSID4060109
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	178.234 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
Solubility in water	Insoluble
Structure
Dipole moment	0 D
Hazards
Safety data sheet	Oxford MSDS
Related compounds
Related compounds	2-Butyne Dimethyl acetylenedicarboxylate
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

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. 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)