Diphenylacetylene

Template:Chembox header | Diphenylacetylene
Diphenylacetylene
Template:Chembox header | General
Systematic name	Diphenylacetylene
Other names	Tolan
Molecular formula	C14H10
SMILES	C(#Cc1ccccc1)c2ccccc2
Molar mass	178.24 g/mol
Appearance	colorless solid
CAS number	501-65-5
Template:Chembox header | Properties
Density and phase	0.990 g/cm³ solid
Solubility in water	insoluble
Other solvents	common organic solvents
Melting point	62.5 °C
Boiling point	0–97 °C/0.3 mmHg
Template:Chembox header | Structure
Molecular shape	sp2 and sp at carbon
Dipole moment	0 D
Template:Chembox header | Hazards
MSDS	External MSDS
Main hazards	innocuous
NFPA 704
Template:Chembox header | Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Template:Chembox header | Related compounds
Related compounds	[[2-butyne|C2Me2 Dimethylacetylenedicarboxylate
Template:Chembox header | Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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 organometallic chemistry.

Preparation

Several preparations for this compound exist:

• one being from benzil which is condensed with hydrazine to give the bis(hydrazone) that in turn suffers oxidation with mercury oxide HgO.
• The compound is usually prepared from stilbene by bromination dehydrohalogenation sequence, but the product can be contaminated with stilbene, which is difficult to remove.
• One methods starts from iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling

Interesting derivatives

• Reaction of Ph₂C₂ with tetraphenyl substituted cyclopentadienone results in the formation of hexaphenylbenzene.
• Reaction of Ph₂C₂ with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.