Thioanisole

Thioanisole
Names
Preferred IUPAC name
(Methylsulfanyl)benzene
Other names
Thioanisole (no longer recommended[1])
Methyl(phenyl)sulfane
Phenyl methyl sulfide
Methylthiobenzene
Identifiers
100-68-5
3D model (Jmol) Interactive image
ChemSpider 7239
EC Number 202-878-2
PubChem 7520
Properties
C7H8S
Molar mass 124.20
Appearance colorless liquid
Density 1.0533 g/cm3
Melting point -15 ºC
Boiling point 193 ºC
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, which is soluble in organic solvents. It is the simplest alkyl-aryl thioether. The name indicates that this compound is the sulfur-analogue of methoxybenzene, anisole.

It can be prepared by methylation of thiophenol.

Reactions

Thioanisole undergoes deprotonation with alkyllithium reagents to afford C6H5SCH2Li, which can be alkylated. The resulting homologated thioether can be manipulated in a variety of ways.[2]

Oxidation of thioanisole gives the chiral sulfoxide.[3]

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-FP001. 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. Carl R. Johnson, Jeffrey E. Keiser "Methyl Phenyl Sulfoxide" Org. Synth. 1966, volume 46, 78. doi:10.15227/orgsyn.046.0078
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