(E)-Stilbene

For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids.
(E)-Stilbene
Names
IUPAC name
1,1'-[(1E)-Ethene-1,2-diyl]dibenzene
Other names
(E)-1,2-Diphenylethene
(E)-Stilbene
trans-Stilbene
trans-1,2-Diphenylethylene
Identifiers
103-30-0 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:36007 YesY
ChEMBL ChEMBL113028 YesY
ChemSpider 553649 YesY
ECHA InfoCard 100.002.817
PubChem 638088
UNII 3FA7NW80A0 N
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
Safety data sheet 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
1
1
0
Flash point >112 °C (234 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

(E)-Stilbene, is the organic compound with the formula (C6H5CH)2. Classified as a diarylethene, it features a central ethene double bond substituted with phenyl groups on each carbon atoms of the double bond. The name stilbene is derived from the Greek word stilbos, which means shining. It is a white solid that dissolves in organic solvents.

Isomers

The isomerization of stilbene under the influence of radiation.

Stilbene exists as two possible isomers. One 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 (41–43 °F), while (E)-stilbene melts around 125 °C (257 °F), illustrating the two compounds are quite different in their physical properties.[1]

Preparation and reactions

Many syntheses have been developed. One popular route entails reduction of benzoin using zinc.[2]

Stilbene undergoes reactions typical of alkenes, being susceptible to bromination, epoxidation, and cycloaddition. Upon irradiation it converts to cis-stilbene, a classic example of a photochemical reaction involving trans-cis isomerization.

Derivatives and uses

Stilbene itself is of little value but serves as a precursor to other derivatives used as dyes, optical brighteners, phosphors, and scintillators. Stilbene is one of the gain mediums used in dye lasers.

4,4′-diamino-2,2′-stilbenedisulfonic acid is a popular optical brightener used in some laundry detergents.
Diethylstilbestrol exhibits estrogenic properties, even though it is not a steroid.

The stilbenoids are naturally occurring stilbene derivatives. Examples include resveratrol and its cousin, pterostilbene. The stilbestrols, which are structurally but not synthetically related to E-stilbene, exhibit estrogenic activity. Members of this group include diethylstilbestrol, fosfestrol, and dienestrol.

References

  1. ↑ Robert E. Buckles and Norris G. Wheeler "cis-Stilbene" Org. Synth. 1953, volume 33, p. 88. doi:10.15227/orgsyn.033.0088
  2. ↑ R. L. Shriner and Alfred Berger "trans-Stilbene" Org. Synth. 1943, volume 23, 86. doi:10.15227/orgsyn.023.0086

Appendix

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

External links

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