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

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,

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

cyclopropenium bromide after the elimination of tert-butoxide.^[6]

doi:10.15227/orgsyn.022.0050
.

doi:10.15227/orgsyn.046.0044
.

doi:10.1021/acs.chemrev.6b00144
.

doi:10.15227/orgsyn.074.0072
.

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