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.

Selenophene
Names
Preferred IUPAC name
Selenophene[1]
Identifiers
103223
ChEBI
ChemSpider
ECHA InfoCard 100.157.009 Edit this at Wikidata
100994
UNII
  • InChI=1S/C4H4Se/c1-2-4-5-3-1/h1-4H
    Key: MABNMNVCOAICNO-UHFFFAOYSA-N
  • C1=C[Se]C=C1
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)
1.58
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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
selenolane
2-selenolene
3-selenolene
Related compounds
furan
thiophene
tellurophene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nomenclature

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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

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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

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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

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  1. ^ 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.
  2. ^ 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.
  3. ^ a b Hartough, H. D. (2009). Thiophene and Its Derivatives. John Wiley & Sons. ISBN 9780470188026.
  4. ^ 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.