2,3-Dihydrothiophene

2,3-Dihydrothiophene
Names
	IUPAC name 2,3-Dihydrothiophene
Identifiers
CAS Number	1120-59-8 [pubchem];
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	120627 ;
PubChem CID	136880;
CompTox Dashboard (EPA)	DTXSID20149809 ;
	InChI InChI=1S/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2 Key: OXBLVCZKDOZZOJ-UHFFFAOYSA-N ; InChI=1/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2 Key: OXBLVCZKDOZZOJ-UHFFFAOYAG;
	SMILES C1CSC=C1; S1\C=C/CC1;
Properties
Chemical formula	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

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]

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]

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References

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

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[1] Shvekhgeimer, M. G. A. (1998). "Dihydrothiophenes. Synthesis and Properties (review)". Chemistry of Heterocyclic Compounds. 34: 1101–1122. doi:10.1007/BF02319487.

[2] Splivallo, R.; Ebeler, S. E. (2015). "Sulfur Volatiles of microbial origin are key contributors to human-sensed truffle aroma". Appl. Microbiol. Biotechnol. 99: 2583–92. doi:10.1007/s00253-014-6360-9. PMID 25573471.