Selenophene
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| Reference =
| PIN = Selenophene{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=141 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}
| OtherNames =
| ImageFileL1= Selenophene Structural Formula V1.svg
| ImageFileR1 = Selenophene-3D-spacefill.png
| ImageFile2 = Selenophene-3D-balls.png
|Section1={{Chembox Identifiers
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| CASNo = 288-05-1
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| ChEBI = 30857
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| ChEMBL =
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| ChemSpiderID = 119907
| ChemSpiderID_Comment =
| KEGG =
| KEGG_Comment =
| PubChem = 136130
| PubChem_Comment =
| SMILES = C1=C[Se]C=C1
| SMILES_Comment =
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| StdInChI =
| StdInChI_Comment =
| StdInChIKey =
| InChI=1S/C4H4Se/c1-2-4-5-3-1/h1-4H
| InChI_Comment =
| InChIKey = MABNMNVCOAICNO-UHFFFAOYSA-N
| UNII = UYZ3M5T8L7
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| Abbreviations =
| Beilstein = 103223
| EC_number =
| EC_number_Comment =
| Gmelin = 100994
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| Section2={{Chembox Properties
| C=4 | H=4 | Se=1
| Appearance = colorless liquid
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| Density = 1.52 g/cm3
| MeltingPtC =-38
| BoilingPtC = 110
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| RefractIndex = 1.58
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| Section7 = {{Chembox Hazards
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| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|301|331|373|410}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+310|303+361+353|304+340|311|314|321|330|370+378|391|403+233|403+235|405|501}}
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| Section8 = {{Chembox Related
| OtherFunction =selenolane
2-selenolene
3-selenolene
| OtherFunction_label = more saturated
| OtherCompounds = furan
thiophene
tellurophene
}}
}}
Selenophene is an organic compound with the chemical formula {{chem2|C4H4Se|auto=1}}. It is an unsaturated compound containing a five-member ring with four carbon atoms and one selenium atom. It is a selenium analog of furan {{chem2|C4H4O}} and thiophene {{chem2|C4H4S}}. A colorless liquid, it is one of the more common selenium heterocycles.
Nomenclature
Atoms in selenophene are numbered sequentially around the ring, starting with the selenium atom as number 1 following normal systematic nomenclature rules. Oxidized forms include selenophene 1,1-dioxide.{{Cite book|doi=10.1016/B978-008044992-0.00313-8|title=Comprehensive Heterocyclic Chemistry III|last=Pelkey|first=E. T.|date=2008|publisher=Elsevier|isbn=9780080449920|editor-last=Katritzky|editor-first=Alan R.|location=Oxford|pages=975–1006|editor-last2=Ramsden|editor-first2=Christopher A.|editor-last3=Scriven|editor-first3=Eric F. V.|editor-last4=Taylor|editor-first4=Richard J. K.}} Related ring structures include those with only one double bond (2-selenolene and 3-selenolene) and the fully saturated structure selenolane.{{cite book|last1=Hartough|first1=H. D.|title=Thiophene and Its Derivatives|date=2009|publisher=John Wiley & Sons|isbn=9780470188026|url=https://books.google.com/books?id=QUgfYi95al4C&pg=PA480|language=en}}
Production
Mazza and Solazzo reported the first confirmed synthesis in 1927. By treating selenium with acetylene and at about 300 °C yields up to 15% selenophene were obtained. Benzoselenophene (analogue of benzothiophene) was also produced.
Substituted selenophenes can be made using a Fiesselman procedure in which a β-chloro-aldehyde reacts with sodium selenide, and then ethyl bromoacetate.{{cite book|last1=Eicher|first1=Theophil|last2=Hauptmann|first2=Siegfried|last3=Speicher|first3=Andreas|title=The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications|date=2013|publisher=John Wiley & Sons|isbn=9783527669868|pages=69–70|url=https://books.google.com/books?id=lAt_Y09iW-4C&pg=PA69|language=en}}