Stilbene

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Stilbene

General
Systematic name	trans-1,2-diphenylethylene (E)-1,2-diphenylethene
Other Names	(E)-stilbene
	trans-stilbene
Molecular formula	C₁₄H₁₂
	C₆H₅CH=CHC₆H₅
SMILES	c1(/C=C/c2ccccc2)ccccc1
Molar mass	180.24928 g/mol
Appearance	Solid
Color	white - slightly beige
CAS number	103-30-0
Properties
Solubility in water	practically insoluble
Melting point	122°C - 125°C
Boiling point	305°C - 307°C
Flash Point	>112°C
Hazards
MSDS	External MSDS
NFPA 704
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references

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

Officially known as trans-1,2-diphenylethylene, aka, stilbene, or more specifically, (E)-stilbene, is the alkene, ethene with two phenyl groups on either carbon of the parent chain. The name was derived from the Greek word stilbos, which means shining. It should also be noted, there is also a (Z)-stilbene which is sterically hindered and less stable because of it. Also notice that (Z)-stilbene has a melting point of 5°C to 6°C, while the melting point of (E)-stilbene is in the 125°C area, this illustrates the significant differences between the two. Because (E)-stilbene is so much more common than (Z)-stilbene, this page will focus only on (E)-stilbene.

Its risk and safety phrases are:

R22 — harmful if swallowed
R37 — irritating to respiratory system
R38 — irritating to skin
R62 — possible risk of impaired fertility
S22 — do not breathe dust
S26A — in case of contact with eyes, rinse immediately with water and seek medical advice
S36 — wear suitable protective clothing
S37 — wear suitable gloves
S45 — in case of accident or if you feel unwell seek medical advice immediately, and show the label if possible

1 Uses of Stilbene
2 Stilbene Reactions
3 More Information
- 3.1 Spectra
4 References
5 External links

[edit] Uses of Stilbene

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.

[edit] Stilbene Reactions

Halogenation of Stilbene
Simple hydrocarbons are relatively unreactive. In order to form more complex molecules, it is generally necessary to introduce more reactive functional groups. Alkenes (olefins) containing the carbon-carbon double bond may be halogenated to form alkyl halides, which are more capable of undergoing further chemical reactions.

An example of halogenation is the bromination of (E)-stilbene. Bromine is somewhat of a special case due in no small part, to its relatively enormous size compared to carbon. Since elemental bromine (Br₂) is volatile and highly corrosive, pyridinium tribromide is commonly used to generate Br₂ in situ.

Greener Halogenation of Stilbene
To green this reaction, the pyridinium tribromide in situ generation of Br₂ is replaced with hydrobromic acid, which is oxidized by hydrogen peroxide(H₂O₂).

2HBr + H₂O₂ → Br₂ + 2H₂O

In either case the halogenation of stilbene is as follows; as seen in the first reaction, the Br-Br bond attracts the attention of the π-bonding electrons (π-bonds being e^- dense and Br being very electronegative), this leads to a weakening and eventual break (heat, plays a crucial role in driving the break forward) of the π-bond. Once the π-bond has been broken, its electrons are transferred to Br₂, causing the Br-Br bond to be severed when the bonding electrons are transferred to the other bromine. At this stage there is the positivly charged intermidiate and the loose bromine ion (Br^-), coming from the opposite direction as the Br₂, the Br^- loosens one of the C-Br Bonds, leaving the final brominated product.

It doesn't matter which stilbene is used for this reaction, (E)-stilbene and (Z)-stilbene will both produce 1,2-dibromo-1,2-diphenylethane. However, bromination of the (Z) isomer results in a racemic mixture of dl stilbene dibromide, while the bromination of an (E) isomer results in a majority meso-stilbene dibromide along with minor amounts of the dl enantiomers. The minor dl product in the bromination of (E)-stilbene is a result of resonance in the bromonium bridge intermediate, where a positive charge is located on one of the two bridge carbons, thus allowing for a syn-addition of a bromine anion.

[edit] More Information

[edit] Spectra

[edit] References

Spectral Database for Organic Compounds, SDBS
(E)-Stilbene on ChemExper
Green Organic Chemistry, Strategies, tools, and Laboratory Experiments. Kenneth M, Doxsee & James E. Hutchison.
Organic Chemistry, Eighth Edition. T.W. Graham Solomonds & Craig B. Fryhle.