Diphenylacetylene
From Wikipedia, the free encyclopedia
| Diphenylacetylene | |
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| 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] |
| 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 |
| Structure | |
| Molecular shape | sp2 and sp at carbon |
| Dipole moment | 0 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | innocuous |
| NFPA 704 | |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | [[2-butyne|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.
Contents |
[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 HgO. [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" Organic Syntheses Collective Volume 4, page 377.
- ^ Fieser, L. F. "Hexaphenylbenzene" Organic Syntheses Collective Volume 5, page 604.
- ^ Xu, R. Breslow, R. "1,2,3-Triphenylcyclopropendium Bromide" Organic Syntheses Collective Volume 9, page 730.
