Thioanisole

Thioanisole
Names
	Preferred IUPAC name (Methylsulfanyl)benzene[1]
	Other names Thioanisole; Methyl(phenyl)sulfane; Phenyl methyl sulfide; Methylthiobenzene
Identifiers
CAS Number	100-68-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	7239;
ECHA InfoCard	100.002.617
EC Number	202-878-2;
PubChem CID	7520;
UNII	BB4K737YF4 ;
CompTox Dashboard (EPA)	DTXSID8059217 ;
	InChI InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3 Key: HNKJADCVZUBCPG-UHFFFAOYSA-N; InChI=1/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3 Key: HNKJADCVZUBCPG-UHFFFAOYAJ;
	SMILES CSC1=CC=CC=C1;
Properties
Chemical formula	C7H8S
Molar mass	124.20 g·mol−1
Appearance	colorless liquid
Density	1.0533 g/cm3
Melting point	−15 °C (5 °F; 258 K)
Boiling point	193 °C (379 °F; 466 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Thioanisole is an organic compound with the formula CH₃SC₆H₅. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkyl–aryl thioether. The name indicates that this compound is the sulfur analogue—the thioether rather than the oxygen-centered ether—of anisole.

It can be prepared by methylation of thiophenol.

Reactions

Alkyllithium reagents deprotonate thioanisole at the methyl group to afford C₆H₅SCH₂Li, a strong nucleophile that can be alkylated to form more complex chains and structures. The resulting homologated thioether can be manipulated in a variety of ways.[2]

Oxidation of sulfur via addition of a single oxygen atom gives methyl phenyl sulfoxide,[3] a reaction useful for titration of oxidants such as dimethyldioxirane.[4] Successive oxidation then leads to the sulfone.

References

Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 707. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
Bailey, Simon "Thioanisole" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. doi:10.1002/047084289X.rt093
Johnson, Carl R.; Keiser, Jeffrey E. (1966). "Methyl Phenyl Sulfoxide". Org. Syntheses. 46: 78. doi:10.15227/orgsyn.046.0078.
Adam, Waldemar; Chan, Yuk Yee; Cremer, Dieter; Gauss, Juergen; Scheutzow, Dieter; Schindler, Michael (1987). "Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations". J. Org. Chem. 52 (13): 2800–2803. doi:10.1021/jo00389a029.

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[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 707. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.

[2] Bailey, Simon "Thioanisole" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. doi:10.1002/047084289X.rt093

[3] Johnson, Carl R.; Keiser, Jeffrey E. (1966). "Methyl Phenyl Sulfoxide". Org. Syntheses. 46: 78. doi:10.15227/orgsyn.046.0078.

[4] Adam, Waldemar; Chan, Yuk Yee; Cremer, Dieter; Gauss, Juergen; Scheutzow, Dieter; Schindler, Michael (1987). "Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations". J. Org. Chem. 52 (13): 2800–2803. doi:10.1021/jo00389a029.