Selenophene
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| Names | |||
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| Preferred IUPAC name
Selenophene[1] | |||
| Identifiers | |||
| 103223 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.157.009 | ||
| 100994 | |||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C4H4Se | |||
| Molar mass | 131.047 g·mol−1 | ||
| Appearance | colorless liquid | ||
| Density | 1.52 g/cm3 | ||
| Melting point | −38 °C (−36 °F; 235 K) | ||
| Boiling point | 110 °C (230 °F; 383 K) | ||
Refractive index (nD)
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1.58 | ||
| Hazards | |||
| GHS labelling: | |||
   
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| Danger | |||
| H225, H301, H331, H373, H410 | |||
| P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P310, P303+P361+P353, P304+P340, P311, P314, P321, P330, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |||
| Related compounds | |||
Related more saturated
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selenolane 2-selenolene 3-selenolene | ||
Related compounds
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furan thiophene tellurophene | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Selenophene is an organic compound with the chemical formula C4H4Se. 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 C4H4O and thiophene C4H4S. A colorless liquid, it is one of the more common selenium heterocycles.
Nomenclature
[edit]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.[2] Related ring structures include those with only one double bond (2-selenolene and 3-selenolene) and the fully saturated structure selenolane.[3]
Production
[edit]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.[3]
Substituted selenophenes can be made using a Fiesselman procedure in which a β-chloro-aldehyde reacts with sodium selenide, and then ethyl bromoacetate.[4]
Properties
[edit]The selenophene molecule is flat.[4] Being aromatic, it undergoes electrophilic substitution reactions. As for thiophene, electrophiles tend to attack at the carbon positions next to the chalcogen. Such reactions are slower than that of furan, but faster than thiophene.[4]
References
[edit]- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 141. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ Pelkey, E. T. (2008). Katritzky, Alan R.; Ramsden, Christopher A.; Scriven, Eric F. V.; Taylor, Richard J. K. (eds.). Comprehensive Heterocyclic Chemistry III. Oxford: Elsevier. pp. 975–1006. doi:10.1016/B978-008044992-0.00313-8. ISBN 9780080449920.
- ^ a b Hartough, H. D. (2009). Thiophene and Its Derivatives. John Wiley & Sons. ISBN 9780470188026.
- ^ a b c Eicher, Theophil; Hauptmann, Siegfried; Speicher, Andreas (2013). The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications. John Wiley & Sons. pp. 69–70. ISBN 9783527669868.