Selenophene
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Names | |||
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Preferred IUPAC name
Selenophene[1] | |||
Identifiers | |||
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103223 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.157.009 ![]() | ||
100994 | |||
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
C4H4Se | |||
Molar mass | 131.047 g·mol−1 | ||
Density | 1.52 | ||
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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Signal word
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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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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). | |||
Infobox references | |||
Selenophene is an unsaturated organic compound containing a five member ring with selenium with formula C4H4Se. It is a metallole with reduced aromatic character compared to thiophene.
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.[2] Related ring structures include those with only one double bond ( and ) and the fully saturated structure .[3]
Production[]
Although Ida Foa claimed to have made selenophene in 1909, the first confirmed production was by Mazza and Solazzo in 1927. They heated acetylene and selenium together at about 300 °C. The selenium burst into flame, and up to 15% selenophene was formed, along with .[3] Another way to make it is from furan heated with hydrogen selenide and aluminium at 400 °C.[4]
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[]
The selenophene molecule is flat and aromatic.[4] Being aromatic, it undergoes electrophilic substitution reactions at the 2- or 2,5-positions.[4] These reactions are slower than that of furan, but faster than thiophene.[4]
References[]
- ^ 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 d e Eicher, Theophil; Hauptmann, Siegfried; Speicher, Andreas (2013). The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications. John Wiley & Sons. pp. 69–70. ISBN 9783527669868.
- Selenium(−II) compounds
- Heterocyclic compounds with 1 ring