Diphenylacetylene
From Wikipedia, the free encyclopedia
| Diphenylacetylene | |
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| IUPAC name | Diphenylacetylene |
| Other names | Tolan |
| Identifiers | |
| CAS number | [501-65-5] |
| SMILES | C(#Cc1ccccc1)c2ccccc2 |
| Properties | |
| Molecular formula | C14H10 |
| Molar mass | 178.24 g/mol |
| Appearance | colorless solid |
| Density | 0.990 g/cm³ solid |
| Melting point |
62.5 °C |
| Boiling point |
0–97 °C/0.3 mmHg |
| Solubility in water | insoluble |
| Structure | |
| Molecular shape | sp2 and sp at carbon |
| Dipole moment | 0 D |
| Hazards | |
| Main hazards | innocuous |
| Related compounds | |
| Related compounds | C2Me2 Dimethylacetylenedicarboxylate |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
[edit] 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.[1]
- 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
[edit] Interesting derivatives
- Reaction of Ph2C2 with tetraphenyl substituted cyclopentadienone results in the formation of hexaphenylbenzene.[2]
- Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.[3]
[edit] References
- ^ Cope, A. C.; Smith, D. S.; Cotter, R. J.. "Phenylacetylene". Org. Synth.; Coll. Vol. 4: 377.
- ^ Fieser, L. F.. "Hexaphenylbenzene". Org. Synth.; Coll. Vol. 5: 604.
- ^ Xu, R. Breslow, R.. "1,2,3-Triphenylcyclopropendium Bromide". Org. Synth.; Coll. Vol. 9: 730.
