Cyclohexanethiol

Cyclohexanethiol
Identifiers
1569-69-3
ChemSpider 14555
Jmol interactive 3D Image
PubChem 15290
Properties
C6H12S
Molar mass 116.22
Appearance colorless liquid
Density 0.95 g/cm3
Boiling point 158 to 160 °C (316 to 320 °F; 431 to 433 K)
low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclohexanethiol is an organosulfur compound with the formula C6H11SH. It is a colorless liquid with a strong odor.

Preparation

It was first prepared by the free-radical reaction of cyclohexane using carbon disulfide as a sulfur source.[1]

It is produced industrially by the hydrogenation of cyclohexanone in the presence of hydrogen sulfide]] over a metal sulfide catalyst:

C6H10O + H2S + H2 → C6H11SH + H2O

It is also obtained by the addition of hydrogen sulfide to cyclohexene in the presence of nickel sulfide.[2]

Safety

The LD50 (oral, rats) is 558/kg.[2]

References

  1. Kharasch, M.S.; Eberly, Kenneth (February 1941). "Reactions of Atoms and Free Radicals in Solution. III. The Introduction of a Mercaptan Group into Cyclohexane". J. Am. Chem. Soc 63 (2): 625. doi:10.1021/ja01847a508. Retrieved 12 April 2015.
  2. 1 2 Kathrin-Maria Roy "Thiols and Organic sulphides" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a26_767
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