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

A15916 Thiophenol, 99+%

Codice CAS
108-98-5
Sinonimi
Benzenethiol
Phenyl mecaptan

Dimensioni Prezzo ($) Quantità Disponibilità
10g 19,40
50g 24,00
250g 56,00
1000g 165,00
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Thiophenol, 99+%

MDL
MFCD00004826
EINECS
203-635-3

Proprietà chimiche

Formula
C6H6S
Peso formula
110.18
Punto di fusione
-15°
Punto di ebollizione
168-169°
Punto di infiammabilità
55°(131°F)
Densità
1.075
Indice di rifrazione
1.5900
Sensibilità
Air Sensitive
Solubilità
Miscible with most organic solvents and aqueous base. Immiscible with water.

Applicazioni

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.

Note

Incompatible with strong acids, bases and oxidizing agents.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): 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.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Merck
14,9355
Beilstein
506523
Classe di rischio
6.1
Gruppo di imballaggio
I
Codice tariffe armonizzato
2930.90
TSCA
Yes
RTECS
DC0525000

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