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Thioanisole

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Thioanisole
Names
Preferred IUPAC name (Methylsulfanyl)benzene
Other names Thioanisole
Methyl(phenyl)sulfane
Phenyl methyl sulfide
Methylthiobenzene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.617 Edit this at Wikidata
EC Number
  • 202-878-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3Key: HNKJADCVZUBCPG-UHFFFAOYSA-N
  • InChI=1/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3Key: HNKJADCVZUBCPG-UHFFFAOYAJ
SMILES
  • CSC1=CC=CC=C1
Properties
Chemical formula C7H8S
Molar mass 124.20 g·mol
Appearance colorless liquid
Density 1.0533 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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.

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

References

  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.
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