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A15916 Thiophenol, 99+%

Numéro de CAS
108-98-5
Synonymes
Benzenethiol
Phenyl mecaptan

Stock No. Conditionnement Prix ($) Quantité Disponibilité
A15916-09 10g 20,30
A15916-18 50g 25,10
A15916-30 250g 58,50
A15916-0B 1000g 172,00
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Thiophenol, 99+%

MDL
MFCD00004826
EINECS
203-635-3

Propriétés chimiques

Formule
C6H6S
Poids moleculaire
110.18
Point de fusion
-15°
Point d'ébullition
168-169°
Point d'éclair
55°(131°F)
Densité
1.075
Indice de réfraction
1.5900
Storage & Sensitivity
Air Sensitive. Store under Nitrogen. Ambient temperatures.
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (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.

Mentions de prudence: 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.

Autres références

Merck
14,9355
Beilstein
506523
Classe de danger
6.1
Groupe d'emballage
I
Code tarifaire harmonisé
2930.90
TSCA
Yes
RTECS
DC0525000

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Analytique et matériel de laboratoire