(E)-Stilbene

For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids.

(E)-Stilbene

Names
IUPAC name (E)-1,2-Diphenylethene
Other names (E)-Stilbene, trans-Stilbene, trans-1,2-Diphenylethylene
Identifiers
CAS Number	103-30-0 Y
ChEBI	CHEBI:36007 Y
ChEMBL	ChEMBL113028 Y
ChemSpider	553649 Y
Jmol 3D model	Interactive image Interactive image
PubChem	638088
InChI InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+ Y Key: PJANXHGTPQOBST-VAWYXSNFSA-N Y InChI=1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+ Key: PJANXHGTPQOBST-VAWYXSNFBV
SMILES c2(\C=C\c1ccccc1)ccccc2 c1ccc(cc1)/C=C/c2ccccc2
Properties
Chemical formula	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)
Solubility in water	Practically insoluble
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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

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.

Preparation and reactions

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

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.

Appendix

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

External links

• (E)-Stilbene on ChemExper