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| Names | |
|---|---|
| IUPAC name (E)-1,2-Diphenylethene | |
| Other names (E)-Stilbene, trans-Stilbene, trans-1,2-Diphenylethylene | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.817 
|
| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
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| Properties | |
| Chemical formula | C14H12 |
| Molar mass | 180.250 g·mol |
| Appearance | Solid |
| Density | 0.9707 g/cm |
| Melting point | 122-125 °C |
| Boiling point | 305-307 °C |
| Solubility in water | Practically insoluble |
| Hazards | |
| NFPA 704 (fire diamond) |
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| Flash point | >112 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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(E)-Stilbene, is a diarylethene, i.e., a hydrocarbon consisting of a trans ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene is derived from the Greek word stilbos, which means shining.
Isomers
Stilbene exists as two possible isomers. The first is trans-1,2-diphenylethylene, called (E)-stilbene or trans-stilbene. The second is cis-1,2-diphenylethylene, called (Z)-stilbene or cis-stilbene, and is sterically hindered and less stable because the steric interactions force the aromatic rings out-of-plane and prevent conjugation. (Z)-Stilbene has a melting point of 5-6 °C, while (E)-stilbene melts around 125 °C, illustrating the two compounds are quite different in their physical properties.
Table 1. Vapor pressures
| Isomer | Temperature, °C | Vapor pressure, kPa |
|---|---|---|
| cis-stilbene | 100 | 0.199 |
| cis-stilbene | 125 | 0.765 |
| cis-stilbene | 150 | 2.51 |
| trans-stilbene | 150 | 0.784 |
Uses
- Stilbene is used in manufacture of dyes and optical brighteners, and also as a phosphor and a scintillator.
- Stilbene is one of the gain mediums used in dye lasers.
- Many stilbene derivates (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.
- Stilbene derivatives especially E(trans) isomer have estrogenic activity so used in making non-steroidal synthetic estrogens such as Diethyl stilbestrol, Fosfosterol, Dienesterol.
Chemistry
- Stilbene will typically have the chemistry of a conjugated alkene, i.e., a diarylethene.
- Trans- and cis-stilbene can interconvert under the influence of light.
References
- Lide, David (1995). CRC Handbook of Chemistry and Physics, 76th edition. USA: CRC Press, Inc. pp. 6–107. ISBN 0-8493-0476-8.
Intercoversion Facts
1)Trans stilbene can be converted to Cis stilbene under influence of UV light.
2)Cis stilbene can be converted to trans stilbene by refluxing cis isomer with Iodine Crystal in presence of high boiler solvent such as DMF.