Thioanisole
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| Names | |
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| Preferred IUPAC name
(Methylsulfanyl)benzene[1] | |
| Other names
Thioanisole
Methyl(phenyl)sulfane Phenyl methyl sulfide Methylthiobenzene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.002.617 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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).
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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.