2,3-Dihydrothiophene

2,3-Dihydrothiophene
Names
	Preferred IUPAC name 2,3-Dihydrothiophene
	Other names 2-Thiolene
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
Density	1.04 g·cm−3 (20 °C)
Melting point	−110 °C (−166 °F; 163 K)
Boiling point	112 °C (234 °F; 385 K)
Refractive index (nD)	1.53 (20 °C)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

2,3-dihydrothiophene is present in dry fermented sausages, a product of the fermentation process. It has a nutty aroma.^[2]

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.^[3]

References

^ ^a ^b Shvekhgeimer, M.-G. A. (October 1998). "Dihydrothiophenes. Synthesis and Properties (review)". Chemistry of Heterocyclic Compounds. 34 (10): 1101–1122. doi:10.1007/BF02319487. S2CID 95679838.
^ Corral, Sara; Leitner, Erich; Siegmund, Barbara; Flores, Mónica (January 2016). "Determination of sulfur and nitrogen compounds during the processing of dry fermented sausages and their relation to amino acid generation". Food Chemistry. 190: 657–664. doi:10.1016/j.foodchem.2015.06.009. hdl:10261/122206.
^ 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.

[Shvekhgeimer1998-1] Shvekhgeimer, M.-G. A. (October 1998). "Dihydrothiophenes. Synthesis and Properties (review)". Chemistry of Heterocyclic Compounds. 34 (10): 1101–1122. doi:10.1007/BF02319487. S2CID 95679838.

[Corral2016-2] Corral, Sara; Leitner, Erich; Siegmund, Barbara; Flores, Mónica (January 2016). "Determination of sulfur and nitrogen compounds during the processing of dry fermented sausages and their relation to amino acid generation". Food Chemistry. 190: 657–664. doi:10.1016/j.foodchem.2015.06.009. hdl:10261/122206.

[3] 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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