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

A15916 Thiophenol, 99+%

Número CAS
Nombre Alternativo
Phenyl mecaptan

Tamaño Precio ($) Cantidad Disponibilidad
10g 19,40
50g 24,00
250g 56,00
1000g 165,00
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Thiophenol, 99+%


Propiedades químicas

Peso molecular
Punto de fusión
Punto de ebullición
Punto de inflamabilidad
Índice de refracción
Air Sensitive
Miscible with most organic solvents and aqueous base. Immiscible with water.


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.


Incompatible with strong acids, bases and oxidizing agents.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H226-H300-H310-H330-H315-H318-H361-H335

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

Indicaciones de precaución: P260-P280-P305+P351+P338-P309-P310a-P302+P352a

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/doctor IF ON SKIN: Wash with plenty of water.

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