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Properties of substance:

methylthiomethyl chloride

Synonyms:

chloromethyl methyl sulfide

Group of substances:

organic

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

C2H5ClS

Structural formula as text:

CH3SCH2Cl

Molar/atomic mass: 96.5791

Boiling point (°C):

110-112

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. 577 [doi: 10.1021/ja01608a016]


C6H5COCl + CH3SOCH3 → C6H5COOH + CH3SCH2Cl

A solution of 11.7 g. (0.15 mole) of methyl sulfoxide in 30 ml. of methylene chloride was added during 30 minutes to a refluxing solution of 45 g. (0.32 mole) of benzoyl chloride in 50 ml. of methylene chloride. The mixture was heated an additional hour and then distilled to yield chloromethyl methyl sulfide, b.p. 103—108°; redistillation gave 7 g. (45%) of material, b.p. 104—106°.

Synthesis 2:

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. 576 [doi: 10.1021/ja01608a016]

A solution of 15.6 g. (0.20 mole) of dimethyl sulfoxide in 20 ml. of methylene chloride was added during 2 hours to a heated solution of 27 g. (0.23 mole) of thionyl chloride in 40 ml. of methylene chloride. The solution was refluxed for an additional hour and distilled giving 17.8 g. (92%) of chloromethyl methyl sulfide, b.p. 104—106°.

Synthesis 3:

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. 577 [doi: 10.1021/ja01608a016]

A solution of 15.6 g. (0.20 mole) of methyl sulfoxide and 27.6 g. (0.20 mole) of benzyl methyl sulfide in 50 ml. of methylene chloride was added to a heated solution of 26.4 g. (0.22 mole) of thionyl chloride in 40 ml. of methylene chloride during 90 minutes. The mixture was distilled, first at atmospheric pressure to yield 8.0 g. (41%) of chloromethyl methyl sulfide, b.p. 104—106°, and then under vacuum giving 12 g. (35%) of ?-chlorobenzyl methyl sulfide, b.p. 125—130° (15 mm.).

Methyl benzyl sulfide when treated alone with thionyl chloride in the above manner gave no sharp boiling product.

Dipole moment (D):

1.68

References:

  1. Ïîêîíîâà Þ.Â. Ãàëîèäñóëüôèäû. - Ë.: ÈËÓ, 1977. - pp. 226 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru