Thioanisole

Thioanisole

Names
Preferred IUPAC name (Methylsulfanyl)benzene
Other names Thioanisole (no longer recommended[1]) Methyl(phenyl)sulfane Phenyl methyl sulfide Methylthiobenzene
Identifiers
CAS Number	100-68-5
3D model (Jmol)	Interactive image
ChemSpider	7239
EC Number	202-878-2
PubChem	7520
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
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