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Cyclohexanethiol

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(Redirected from Cyclohexyl mercaptan)
Cyclohexanethiol
Names
Preferred IUPAC name Cyclohexanethiol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.890 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H12S/c7-6-4-2-1-3-5-6/h6-7H,1-5H2Key: CMKBCTPCXZNQKX-UHFFFAOYSA-N
  • InChI=1/C6H12S/c7-6-4-2-1-3-5-6/h6-7H,1-5H2Key: CMKBCTPCXZNQKX-UHFFFAOYAW
SMILES
  • C1CCC(CC1)S
Properties
Chemical formula C6H12S
Molar mass 116.22 g·mol
Appearance Colorless liquid
Density 0.95 g/cm
Boiling point 158 to 160 °C (316 to 320 °F; 431 to 433 K)
Solubility in water Low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cyclohexanethiol is a thiol 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.

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.

Safety

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

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.
  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.
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