2,3-Dihydrothiophene

2,3-Dihydrothiophene is a heterocyclic compound and an organosulfur compound with the formula SC4H6. It is isomeric with the more symmetrical 2,5-dihydrothiophene. Both isomers of dihydrothiophene are colorless liquids with a thioether-like odor. In terms of their reactivity, both isomers exhibit characteristics of alkenes and thioethers, undergoing addition reactions at carbon and oxidation at sulfur. In contrast, thiophene engages in neither reaction.[1]

2,3-Dihydrothiophene
Names
Preferred IUPAC name
2,3-Dihydrothiophene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2 checkY
    Key: OXBLVCZKDOZZOJ-UHFFFAOYSA-N checkY
  • InChI=1/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2
    Key: OXBLVCZKDOZZOJ-UHFFFAOYAG
  • C1CSC=C1
  • S1\C=C/CC1
Properties
C4H6S
Molar mass 86.16 g/mol
Appearance colorless liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dihydrothiophenes in nature

Dihydrothiophenes contribute to the aroma of the white truffle. The major component is 3-methyl-4,5-dihydrothiophene (alternative name:4-methyl-2,3-dihydrothiophene), produced by bacterial colonies in the truffle's fruiting bodies.[2]

References
  1. Shvekhgeimer, M. G. A. (1998). "Dihydrothiophenes. Synthesis and Properties (review)". Chemistry of Heterocyclic Compounds. 34 (10): 1101–1122. doi:10.1007/BF02319487. S2CID 95679838.
  2. Splivallo, R.; Ebeler, S. E. (2015). "Sulfur Volatiles of microbial origin are key contributors to human-sensed truffle aroma". Appl. Microbiol. Biotechnol. 99 (6): 2583–92. doi:10.1007/s00253-014-6360-9. PMID 25573471. S2CID 16749990.


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