Cyclohexanethiol

Cyclohexanethiol
Identifiers
CAS Number	1569-69-3;
3D model (JSmol)	Interactive image;
ChemSpider	14555;
ECHA InfoCard	100.014.890
PubChem CID	15290;
CompTox Dashboard (EPA)	DTXSID2027416 ;
	InChI 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;
	SMILES C1CCC(CC1)S;
Properties
Chemical formula	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)
Solubility in water	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]

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

^ 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.
^ ^a ^b 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