Diphenylacetylene

Diphenylacetylene
Names
	Preferred IUPAC name 1,1′-Ethynediyldibenzene
	Other names Tolane; 1,2-Diphenylethyne; Diphenylethyne; 2-Phenylethynylbenzene; Tolan
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
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 (SDS)	Fisher Scientific 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). verify (what is ?) 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 involves the coupling of iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene.

Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers.^[1]

Reaction of diphenylacetylene with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene in a Diels–Alder reaction.^[4]

Dicobalt octacarbonyl catalyzes alkyne trimerisation of diphenylacetylene to form hexaphenylbenzene.^[5]

Reaction of Ph₂C₂ with benzal chloride in the presence of potassium t-butoxide affords 3-tert-butoxy-1,2,3-triphenylcyclopropene, which converts to 1,2,3-triphenylcyclopropenium bromide after the elimination of tert-butoxide.^[6]

^ ^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.
^ Cope, A. C.; Smith, D. S.; Cotter, R. J. (1954). "Diphenylacetylene". Organic Syntheses. 34: 42. doi:10.15227/orgsyn.034.0042.
^ Lee Irvin Smith; M. M. Falkof (1942). "Diphenylacetylene". Organic Syntheses. 22: 50. doi:10.15227/orgsyn.022.0050.
^ Fieser, L. F. (1966). "Hexaphenylbenzene". Organic Syntheses. 46: 44. doi:10.15227/orgsyn.046.0044.
^ Vij, V.; Bhalla, V.; Kumar, M. (8 August 2016). "Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold". Chemical Reviews. 116 (16): 9565–9627. doi:10.1021/acs.chemrev.6b00144.
^ Xu, Ruo; Breslow, Ronald (1997). "1,2,3-Triphenylcyclopropenium Bromide". Organic Syntheses. 74: 72. doi:10.15227/orgsyn.074.0072.