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108-98-5 - Thiophenol, 99+% - Benzenethiol - Phenyl mecaptan - A15916 - Alfa Aesar

A15916 Thiophenol, 99+%

CAS Number
108-98-5
Synonyms
Benzenethiol
Phenyl mecaptan

Size Price ($) Quantity Availability
10g 19.26
50g 23.90
250g 56.26
1000g 163.77
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Thiophenol, 99+%

MDL
MFCD00004826
EINECS
203-635-3

Chemical Properties

Formula
C6H6S
Formula Weight
110.18
Melting point
-15°
Boiling Point
168-169°
Flash Point
55°(131°F)
Density
1.075
Refractive Index
1.5900
Sensitivity
Air Sensitive
Solubility
Miscible with most organic solvents and aqueous base. Immiscible with water.

Applications

Thiophenol acts as a reagent to synthesize alfa, beta-unsaturated sulfides, beta-lactones and (3H-benzo[c][1,2]diselenol-3-yl)(phenyl)sulfane. It is used as an antinematodal agent and an intermediate in the preparation of sodium thiophenolate, pentachlorothiophenol and alkyl phenylsulfides. It acts as an inhibitor of human fibroblast collagenase in vitro.

Notes

Incompatible with strong acids, bases and oxidizing agents.

Literature References

For a detailed investigation of alkylation using, e.g. K2CO3 in acetone, see: Synth. Commun., 22, 1691 (1992). Unactivated aryl chlorides undergo nucleophilic substitution in the presence of K2CO3 in NMP to give aryl sulfides: J. Org. Chem., 56, 862 (1991).

Michael additions occur readily with electron deficient alkenes. Subsequent chlorination with NCS and dehydrochlorination provides a stereoselective route to vinyl thioethers: J. Org. Chem., 46, 235 (1981):

The Cu(I) derivative, phenylthiocopper forms complexes with alkyllithiums, which are useful alkyl transfer reagents, undergoing conjugate addition to enones, coupling with alkyl iodides to alkanes, and converting acid halides to ketones: J. Am. Chem. Soc., 95, 7788 (1973); Synthesis, 662 (1974); Org. Synth. Coll., 6, 248 (1988).

Chlorination of PhSH with NCS: J. Org. Chem., 37, 1367 (1972), or SO2Cl2: Org. Synth. Coll., 8, 550 (1993), gives the useful reagent benzenesulfenyl chloride, PhSCl.

Dilithiation of PhSH with n-BuLi and TMEDA gives exclusive ortho-metallation: J. Am. Chem. Soc., 111, 654, 665, 2327 (1989). Subsequent treatment of the dilithio species with DMF, followed by in situ reaction with chloroacetone provides a useful route to the benzo[b]thiophene system: J. Org. Chem., 58, 1293 (1993):

Interception of the DMF adduct provides a source of the unstable 2-mercaptobenzaldehyde. Alternatively, ortho-metallated thiophenols can be formed by lithiation of the THP ether, in which coordination by oxygen favors ortho-lithiation: J. Am. Chem. Soc., 111, 658 (1989).

Dhakshinamoorthy, A.; Primo, A.; Esteve-Adell, I.; Alvaro, M.; Garcia, H. Boron Nitride Nanoplatelets as a Solid Radical Initiator for the Aerobic Oxidation of Thiophenol to Diphenyldisulfide. ChemCatChem 2015, 7 (5), 776-780.

Reva, I.; Nowak, M. J.; Lapinski, L.; Fausto, R. Hydrogen atom transfer reactions in thiophenol: photogeneration of two new thione isomers. Phys. Chem. Chem. Phys. 2015, 17 (7), 4888-4898.

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H310-H330-H315-H335-H318-H226-H361

Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes skin irritation. May cause respiratory irritation. Causes serious eye damage. Flammable liquid and vapour. Suspected of damaging fertility or the unborn child.

Precautionary Statements: P260-P280-P305+P351+P338-P309-P310-P302+P352

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water.

Other References

Merck
14,9355
Beilstein
506523
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
DC0525000

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