(E)-Stilbene

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For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids.
(E)-Stilbene
trans-stilbene - skeletal formula
trans-stilbene - ball-and-stick model
Names
IUPAC name
(E)-1,2-Diphenylethene
Other names
(E)-Stilbene, trans-Stilbene, trans-1,2-Diphenylethylene
Identifiers
103-30-0 YesY
ChEBI CHEBI:36007 YesY
ChEMBL ChEMBL113028 YesY
ChemSpider 553649 YesY
Jmol-3D images Image
Image
PubChem 638088
Properties
C14H12
Molar mass 180.25 g·mol−1
Appearance Solid
Density 0.9707 g/cm3
Melting point 122 to 125 °C (252 to 257 °F; 395 to 398 K)
Boiling point 305 to 307 °C (581 to 585 °F; 578 to 580 K)
Practically insoluble
Hazards
MSDS External MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point >112 °C (234 °F)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

(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[edit]

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.[citation needed] (Z)-Stilbene has a melting point of 5–6 °C (41–43 °F), while (E)-stilbene melts around 125 °C (257 °F), illustrating the two compounds are quite different in their physical properties.

Table 1. Vapor pressures[1]

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[edit]

Chemistry[edit]

  • 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[edit]

  1. ^ Lide, David (1995). CRC Handbook of Chemistry and Physics, 76th edition. USA: CRC Press, Inc. pp. 6–107. ISBN 0-8493-0476-8. 

External links[edit]