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Properties of substance:

thietane

Synonyms:

trimethylene sulfide

Group of substances:

organic

Physical appearance:

liquid

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

C3H6S

Structural formula as text:

(CH2)3S

Molar/atomic mass: 74.145

Melting point (°C):

-73.24

Boiling point (°C):

95

CAS №: 287-27-4

Solubility (g/100 g of solvent):

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

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]


ClCH2CH2CH2Br + (H2N)2CS + 2NaOH → (CH2)3S + NaCl + NaBr + 2NH3 + CO2

Thiacyclobutane was obtained by the addition of 394 g. (2.5 moles) of 1-bromo-3-chloropropane during one hour to a heated and well-stirred solution of 228 g. (3.0 moles) of thiourea and 360 g. (9 moles) of sodium hydroxide in 1500 ml. of water. After two additional hours at reflux with vigorous stirring the mixture was steam distilled. After separation of the sulfide layer and drying over anhydrous potassium carbonate, distillation gave 84 g (45% yield) of thiacyclobutane, b.p. 92—94°.

References:

  1. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010. - pp. 3-484
  2. Химия: справочное руководство. - Под ред. Гаврюченкова Ф.Г., Курочкиной М.И. и др. - Л.: Химия, 1975. - pp. 361 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru