Names | |
---|---|
Preferred IUPAC name
1,1′-Ethynediyldibenzene | |
Other names
Tolane
1,2-Diphenylethyne Diphenylethyne 2-Phenylethynylbenzene Tolan | |
Identifiers | |
3D model (
JSmol)
|
|
606478 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.206 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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 |
Insoluble | |
Structure | |
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).
|
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.
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-triphenyl cyclopropene, which converts to 1,2,3-triphenyl cyclopropenium bromide after the elimination of tert-butoxide. [6]
Names | |
---|---|
Preferred IUPAC name
1,1′-Ethynediyldibenzene | |
Other names
Tolane
1,2-Diphenylethyne Diphenylethyne 2-Phenylethynylbenzene Tolan | |
Identifiers | |
3D model (
JSmol)
|
|
606478 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.206 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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 |
Insoluble | |
Structure | |
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).
|
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.
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-triphenyl cyclopropene, which converts to 1,2,3-triphenyl cyclopropenium bromide after the elimination of tert-butoxide. [6]