Thioanisole

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

Thioanisole
Thioanisol.svg
Names
Preferred IUPAC name
(Methylsulfanyl)benzene[1]
Other names
Thioanisole
Methyl(phenyl)sulfane
Phenyl methyl sulfide
Methylthiobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.617
EC Number
  • 202-878-2
UNII
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).
Infobox references

It can be prepared by methylation of thiophenol.

ReactionsEdit

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.

ReferencesEdit

  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.