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(Z)-Stilbene
Names


IUPAC name cis-1,2-Diphenylethylene
Preferred IUPAC name (Z)-1,2-Diphenylethene
Other names cis-Stilbene
Identifiers
CAS Number	645-49-8
3D model (JSmol)	Interactive image
Beilstein Reference	1616739
ChEBI	CHEBI:36008
ChEMBL	ChEMBL393702
ChemSpider	4512351
ECHA InfoCard	100.010.406
EC Number	211-445-7
Gmelin Reference	4380
PubChem CID	5356785
UNII	TTG5048Y3K
CompTox Dashboard (EPA)	DTXSID5026049
InChI InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11-Key: PJANXHGTPQOBST-QXMHVHEDSA-N 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-QXMHVHEDBW
SMILES c2(\C=C/c1ccccc1)ccccc2
Properties
Chemical formula	C₁₄H₁₂
Molar mass	180.250 g·mol
Appearance	Liquid
Melting point	5 to 6 °C (41 to 43 °F; 278 to 279 K)
Boiling point	307 °C (585 °F; 580 K) at 1 atm (82°C to 84°C at 0.4 mmHg)
Solubility in water	Practically insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Safety data sheet (SDS)	Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

(Z)-Stilbene is a diarylethene, that is, a hydrocarbon consisting of a cis ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene was derived from the Greek word stilbos, which means shining.

Isomers

Stilbene exists as two possible isomers known as (E)-stilbene and (Z)-stilbene. (Z)-Stilbene is sterically hindered and less stable because the steric interactions force the aromatic rings 43° 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 that the two compounds are quite different.

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.

Properties

Stilbene will typically have the chemistry of a diarylethene, a conjugated alkene.
Stilbene can undergo photoisomerization under the influence of UV light.
Stilbene can undergo stilbene photocyclization, an intramolecular reaction.
(Z)-Stilbene can undergo electrocyclic reactions.

Natural occurrence

Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.

References

"cis-Stilbene". pubchem.ncbi.nlm.nih.gov. Retrieved 5 December 2021.
Eliel, Ernest L.; Wilen, Samuel H. (1994). Stereochemistry of Organic Compounds. John Wiley and Sons. pp. 566–567. ISBN 0-471-01670-5.

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