9355. Thiophenol

Nomenclature

CAS number: 108-98-5
Benzenethiol; phenylmercaptan; phenylthiol.
C6H6S; mol wt 110.18.
C 65.41%, H 5.49%, S 29.10%.

Description and references

Prepd by the reduction of benzenesulfonyl chloride with zinc dust in sulfuric acid: Adams, Marvel, Org. Synth. 1, 71 (1921).

Chemical structure

Properties

Liquid. Repulsive, penetrating, garlic-like odor, esp when impure. d425 1.0728; bp760 168.3°; bp100 103.6°; bp50 86.2°; bp20 69.7°; bp1.0 18.6°; nD25 1.58603. Heat of fusion 24.90 cal/g; spec heat at 25°: 0.3829; entropy at 25°: 52.6. Insol in water. Very sol in alc; miscible with ether, benzene, CS2. Feebly acidic. Oxidizes in air, esp when dissolved in alcoholic ammonia, forming diphenyl disulfide, C6H5SSC6H5. The hydrogen of the SH group is easily replaced by metals.

Caution

Potential symptoms of overexposure are irritation of eyes, skin and respiratory system; dermatitis; cyanosis; coughing, wheezing, dyspnea, pulmonary edema, pneumonitis; headache, dizziness, CNS depression; nausea, vomiting; kidney, liver and spleen damage. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 26.