Thiophenol

Structural formula
General
Surname	Thiophenol
other names	Phenyl mercaptan Benzenethiol Benzenthiol ( IUPAC )
Molecular formula	C 6 H 6 S
Brief description	colorless liquid with an unpleasant odor
External identifiers / databases
CAS number 108-98-5 EC number 203-635-3 ECHA InfoCard 100.003.306 PubChem 7969 Wikidata Q338965
properties
Molar mass	110.18 g mol −1
Physical state	liquid
density	1.08 g cm −3 (20 ° C)
Melting point	−15 ° C
boiling point	169 ° C
Vapor pressure	1.5 h Pa (20 ° C)
pK s value	6.62 (25 ° C)
solubility	very bad in water (0.94 g l −1 at 20 ° C) soluble in ethanol, diethyl ether and benzene
Refractive index	1.5893 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-300 + 310 + 330-315-318-335-361-371-373-410 P: 210-260-280-301 + 310 + 330-302 + 352-304 + 340-305 + 351 + 338-310-403 + 233
MAK	Switzerland: 0.5 ml m −3 or 2.3 mg m −3
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

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

Extraction

Among other things, thiophenol can be produced by:

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

properties

Thiophenol has the formula C ₆ H ₅ -SH. At room temperature it is a moderately volatile, but extremely foul-smelling and toxic liquid. Thiophenols are more acidic than phenols , the corresponding oxygen compounds.

Reactions

With alkyl iodides, thioethers result. Oxidation produces diphenyl disulfide , which can be reduced back to thiophenol with sodium borohydride . Therefore, thiophenol can serve as a source of hydrogen in chemical reactions. Phenylsulfenyl chloride is formed with chlorine . The reaction of thiophenol with alkali hydroxides ( sodium hydroxide , potassium hydroxide ) produces the corresponding salts ( thiophenolates ). The reaction with carboxylic acid chlorides in the presence of bases such as triethylamine results in thiol esters .

Accidents

On the night of February 16, 2011, around 30 liters of thiophenol were released on the premises of a forwarding company in Homberg (Efze) in northern Hesse . About 180 people were contaminated with the fumes, 101 of them had to be taken to hospital.

See also

Thiophenol is formally the monomer of polyphenylene sulfide , but it is not produced industrially from the monomer.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on thiophenol in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-45.
3. ^ Brockhaus ABC chemistry. VEB FA Brockhaus Verlag, Leipzig 1965, p. 1411.
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-36.
5. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 108-98-5 or thiophenol ), accessed on November 2, 2015.
6. ^ R. Adams, CS Marvel: Thiophenol In: Organic Syntheses . 1, 1921, p. 71, doi : 10.15227 / orgsyn.001.0071 ; Coll. Vol. 1, 1941, p. 504 ( PDF ).
7. ↑ O. Campo Piano: thiophenol. In: L. Paquette (Ed.): Encyclopedia of Reagents for Organic Synthesis J. Wiley & Sons, New York 2004.
8. ↑ AGM Barrett, D. Dhanak, GG Graboski, SJ Taylor: (Phenylthio) nitromethane In: Organic Syntheses . 68, 1990, p. 8, doi : 10.15227 / orgsyn.068.0008 ; Coll. Vol. 8, 1993, p. 550 ( PDF ).
9. ↑ Gerd Buchholz, Jürgen Martens, Klaus Praefcke : 2- and 4-azathioxanthones by photo rearrangement of thionicotinic acid S-aryl esters. In: Angewandte Chemie. Volume 86, 1974, p. 562; Angewandte Chemie International Edition English. Volume 13, 1974, p. 550.
10. ↑ Major alarm and more than 30 injured in a poison accident. In: faz.net , February 16, 2011. (faz.net)
11. ↑ Dangerous Goods Accident number of injured rises to 101 on: nh24.de . (nh24.de ( Memento of the original from February 19, 2011 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this note. , accessed on February 17, 2011 .)