Cyclohexanethiol is a

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

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 Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohex ...

using

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical ...

as a sulfur source. It is produced industrially by the hydrogenation of

cyclohexanone Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohex ...

in the presence of

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The und ...

over a metal sulfide

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

: :C₆H₁₀O + H₂S + H₂ → C₆H₁₁SH + H₂O It is also obtained by the addition of

cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light a ...

in the presence of

nickel sulfide Nickel sulfide is any inorganic compound with the formula NiSx. They range in color from bronze (Ni3S2) to black (NiS2). The nickel sulfide with simplest stoichiometry is NiS, also known as the mineral millerite. From the economic perspective, ...

.Kathrin-Maria Roy "Thiols and Organic sulphides" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2002, Wiley-VCH Verlag, Weinheim.

Safety

The (injected, mice) was estimated at 316 mg/kg by the

United States Department of Health, Education, and Welfare The United States Department of Health and Human Services (HHS) is a cabinet-level executive branch department of the U.S. federal government created to protect the health of all Americans and providing essential human services. Its motto is ...

References

{{Reflist Cyclohexyl compounds Thiols Foul-smelling chemicals