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Properties of substance:

methyl phenyl sulfide

Synonyms:

thioanisole

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C7H8S

Structural formula as text:

C6H5SCH3

Boiling point (°C):

194.3

Solubility (g/100 g of solvent):

acetone: very soluble [Ref.]
ethanol: soluble [Ref.]
water: insoluble [Ref.]

Density:

1.0579 (20°C, g/cm3)

Synthesis 1:

Reference: Bordwell, F. G., Pitt, B. M. The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides / Journal of the American Chemical Society. - 1955. - Vol. 77, No. 3 pp. 575 [doi: 10.1021/ja01608a016]

A solution of 39.6 g. (0.25 mole) of chloromethyl phenyl sulfide in 100 ml. of ether was added during 30 minutes to the Grignard reagent prepared from 47.5 g. (0.58 mole) of t-butyl chloride and 13 g. of magnesium in 300 ml. of ether. The mixture was heated for 30 minutes, the gas evolved being trapped in a Dry Ice trap containing pentane. Titration of the contents of the trap with bromine in carbon tetrachloride indicated the formation of 17% of isobutylene. After standing overnight the reaction mixture was hydrolized with water to yield on distillation 9.5 g. (30%) of methyl phenyl sulfide, b.p. 82—84° (16 mm.), together with 5.2 g. of product, b.p. 121—123° (16 mm.), which was not characterized. The identity of the methyl phenyl sulfide was established by carrying out a mixed m.p. determination with the sulfone (m.p. 87.5—88°, prepared by oxidation) and an authentic sample.

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-398

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru