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Cyclohexanethiol

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(Redirected from Cyclohexyl mercaptan)
Cyclohexanethiol
Names
Preferred IUPAC name
Cyclohexanethiol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.890 Edit this at Wikidata
UNII
  • InChI=1S/C6H12S/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
    Key: CMKBCTPCXZNQKX-UHFFFAOYSA-N
  • InChI=1/C6H12S/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
    Key: CMKBCTPCXZNQKX-UHFFFAOYAW
  • C1CCC(CC1)S
Properties
C6H12S
Molar mass 116.22 g·mol−1
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).

Cyclohexanethiol is a thiol with the formula C6H11SH. It is a colorless liquid with a strong odor.

Preparation

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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

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The LD50 (injected, mice) was estimated at 316 mg/kg by the United States Department of Health, Education, and Welfare.[3]

References

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  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.
  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
  3. ^ Occupational Exposure to N-alkane Mono Thiols, Cyclohexanethiol, and Benzenethiol. U.S. Government Printing Office. 1978.