| Revision as of 15:56, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 458760612 of page (Z)-Stilbene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 06:46, 17 November 2023 edit Nucleus hydro elemon (talk | contribs)Extended confirmed users3,331 edits Added {{More citations needed}} tagTag: Twinkle |
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{{More citations needed|date=November 2023}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{DISPLAYTITLE:(''Z'')-Stilbene}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 443239349 |
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|verifiedrevid = 477201195 |
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| Name = (''Z'')-Stilbene |
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|Name = (''Z'')-Stilbene |
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| ImageFile = Stilbene_cis_structure.svg |
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|ImageFile = Stilbene_cis_structure.svg |
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|ImageFile1 = (Z)-Stilbene-3D-spacefill.png |
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| IUPACName = ''cis''-1,2-Diphenylethylene<br /> |
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|ImageName1 = C=black, H=white |
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(''Z'')-1,2-Diphenylethene |
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| OtherNames = ''cis''-Stilbene |
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|ImageAlt1 = (Z)-Stilbene molecule |
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|IUPACName = ''cis''-1,2-Diphenylethylene |
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| Section1 = {{Chembox Identifiers |
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|PIN = (''Z'')-1,2-Diphenylethene |
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| InChI = 1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- |
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|OtherNames = ''cis''-Stilbene |
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| InChIKey = PJANXHGTPQOBST-QXMHVHEDBW |
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|Section1={{Chembox Identifiers |
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| PubChem = 5356785 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 645-49-8 |
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| ChEMBL = 393702 |
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|Beilstein = 1616739 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChI = 1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- |
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|ChEMBL = 393702 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = PJANXHGTPQOBST-QXMHVHEDSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CASNo = 645-49-8 |
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|ChEBI = 36008 |
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|ChemSpiderID = 4512351 |
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| EINECS =211-445-7 |
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|EC_number = 211-445-7 |
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| SMILES = c2(\C=C/c1ccccc1)ccccc2 |
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|Gmelin = 4380 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PubChem = 5356785 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEBI = 36008 |
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|UNII = TTG5048Y3K |
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| ChemSpiderID = 4512351 |
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|InChI = 1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- |
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}} |
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|InChIKey = PJANXHGTPQOBST-QXMHVHEDBW |
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| Section2 = {{Chembox Properties |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| C=14 | H=12 |
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|StdInChI = 1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- |
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| Appearance = Liquid |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Solubility = Practically insoluble |
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|StdInChIKey = PJANXHGTPQOBST-QXMHVHEDSA-N |
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| MeltingPt = 5-6 °C |
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|SMILES = c2(\C=C/c1ccccc1)ccccc2 |
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| BoilingPt = 82–84 °C at 0.4 mmHg |
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}} |
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| Section7 = {{Chembox Hazards |
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| RPhrases = {{R36}} {{R38}} |
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| SPhrases = {{S26}} {{S36}} |
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| ExternalMSDS = }} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|C=14 | H=12 |
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|Appearance = Liquid |
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|Solubility = Practically insoluble |
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|MeltingPtC = 5 to 6 |
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|BoilingPtC = 307 |
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|BoilingPt_notes = at 1 atm (82°C to 84°C at 0.4 mmHg) |
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}} |
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|Section7={{Chembox Hazards |
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| Hazards_ref=<ref>{{cite web |title=cis-Stilbene |url=https://pubchem.ncbi.nlm.nih.gov/compound/5356785#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=5 December 2021 |language=en}}</ref> |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|315|319}} |
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|PPhrases = {{P-phrases|264|280|302+352|305+351+338|321|332+313|337+313|362}} |
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|ExternalSDS = }} |
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}} |
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'''(''Z'')-Stilbene''' is a ], that is, a ] consisting of a cis ] double bond substituted with a ] group on both carbon atoms of the double bond. The name stilbene was derived from the ] word {{lang|grc|stilbos}}, which means shining. |
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==Isomers== |
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Stilbene exists as two possible isomers known as ] and (''Z'')-stilbene. (''Z'')-Stilbene is ] and less stable because the steric interactions force the aromatic rings 43° out-of-plane and prevent ].<ref>{{cite book |last1=Eliel |first1=Ernest L. |authorlink1 =Ernest L. Eliel |last2=Wilen |first2=Samuel H. |title=Stereochemistry of Organic Compounds |date=1994 |publisher=John Wiley and Sons |isbn=0-471-01670-5 |pages=566–567}}</ref> (''Z'')-Stilbene has a melting point of {{convert|5|-|6|C}}, while (''E'')-stilbene melts around {{convert|125|C}}, illustrating that the two compounds are quite different. |
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==Uses== |
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* Stilbene is used in manufacture of ]s and ]s, and also as a ] and a ]. |
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* Stilbene is one of the ]s used in ]s. |
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==Properties== |
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* Stilbene will typically have the chemistry of a ], a conjugated ]. |
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* Stilbene can undergo ] under the influence of UV light. |
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* Stilbene can undergo ], an ]. |
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* (Z)-Stilbene can undergo ]s. |
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==Natural occurrence== |
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Many stilbene derivatives (]s) are present naturally in plants. An example is ] and its cousin, ]. |
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==References== |
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{{Reflist}} |
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{{DEFAULTSORT:Stilbene, (Z)-}} |
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] |
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] |
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] |
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] |
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] |
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] |