Thiophenol

Phenyl mercaptan, thiophenol

Colorless liquid with an unpleasant odor

Liquid

1.08 g · cm -3 ( 20 ° C)

-15 ° C

169 ° C

1.5 hPa ( 20 ° C)

6.62 (25 ° C)

• Very poor in water ( 0.94 g · l-1 at 20 ° C)
• Soluble in ethanol, diethyl ether and benzene

1.5893 (20 ° C)

Risk

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Thiophenol is an organic sulfur compound, a colorless, toxic liquid malodor. It is an important starting material for organic synthesis. Thiophenols are a group of compounds having a thiol group on a benzene ring (-SH).

Extraction

Thiophenol may be prepared inter alia by:

• Reduction of benzenesulfonyl chloride with zinc
• Aerating phenyl Grignard or phenyllithium compound with sulfur and subsequent acidification

Properties

Thiophenol has the formula C6H5 -SH. It is at room temperature before as moderately volatile but extremely malodorous and toxic liquid. Thiophenols are more acidic than phenols, the corresponding oxygen compounds.

Reactions

With alkyl iodide to yield thioether oxidation produces diphenyl disulfide, which can be reduced back to thiophenol with sodium borohydride. Therefore thiophenol can be used in chemical reactions as a source of hydrogen. With chlorine results phenylsulfenyl. The reaction of thiophenol with alkali (sodium hydroxide, potassium hydroxide), the corresponding salts formed ( thiophenolates ). In the reaction with carboxylic acid chlorides in the presence of bases such as triethylamine arise thiolester.

Accidents

On the night of February 16, 2011, around 30 liters of thiophenol on the site of a company in the North Hessian Homberg ( Efze) were released from carelessness. To the 180 people were contaminated with vapors, 101 of which had to be taken to hospital.