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100-68-5 - Thioanisole, 99% - Methyl phenyl sulfide - A14846 - Alfa Aesar

A14846 Thioanisole, 99%

Codice CAS
100-68-5
Sinonimi
Methyl phenyl sulfide

Dimensioni Prezzo ($) Quantità Disponibilità
25g 22,50
100g 38,10
500g 134,00
2500g 562,00
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Thioanisole, 99%

MDL
MFCD00008559
EINECS
202-878-2

Proprietà chimiche

Formula
C7H8S
Peso formula
124.21
Punto di fusione
-15°
Punto di ebollizione
188-189°
Punto di infiammabilità
73°(163°F)
Densità
1.058
Indice di rifrazione
1.5860
Solubilità
Miscible with most common organic solvents. Immiscible with water.

Applicazioni

Thioanisole is used as an intermediate in the preparation of dyes, pharmaceuticals and agrochemicals. It is also used to prepare stable sulfonium salts, sulfoxides and sufones. It is utilized for the cleavage of methyl ethers in association with triflic acid. It acts as a flavoring agent or an adjuvant. It is an important starting material for the synthesis of 3-substituted benzo[b]thiophenes.

Note

Incompatible with strong oxidizing agents.

Letteratura

Monolithiation is thought to occur initially on the ring, but rearrangement then gives the more stable phenylthiomethyllithium: J. Org. Chem., 31, 4097 (1966); Tetrahedron Lett., 1961 (1977). Further metallation occurs at the ortho-position. See, e.g.: Tetrahedron, 46, 861 (1990). Demetallation and acylation is the basis of a route to 3-substituted benzo[b]thiophenes: Synthesis, 888 (1988):

Cation scavenger in the acidic deprotection of peptides; see, e.g.: Int. J. Pept. Prot. Res., 36, 255 (1990). See Appendix 6. The combination of the soft nucleophile thioanisole and the hard acid triflic acid has been used for the cleavage of methyl ethers, e.g. O-methyltyrosine, resistant to other methods: J. Chem. Soc., Chem. Commun., 971 (1979). The same conditions have been used for the cleavage of Cbz, Boc, benzyl and 4-methoxybenzyl protecting groups in peptide synthesis: Chem. Pharm. Bull., 28, 1214 (1980); 29, 600 (1981); J. Chem. Soc., Chem. Commun., 101 (1980); see also: Angew. Chem. Int. Ed., 33, 1729 (1994).

Trehoux, A.; Roux, Y.; Guillot, R.; Mahy, J. P.; Avenier, F. Catalytic oxidation of dibenzothiophene and thioanisole by a diiron(III) complex and hydrogen peroxide. J. Mol. Catal. A: Chem. 2015, 396, 40-46.

Li, S. L.; Xu, X.; Truhlar, D. G. Computational simulation and interpretation of the low-lying excited electronic states and electronic spectrum of thioanisole. Phys. Chem. Chem. Phys. 2015, 17 (31), 20093-20099.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227-H302-H315-H319-H317

Combustible liquid. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction.

Dichiarazioni precauzionali: P210u-P261-P280a-P280a-P305+P351+P338-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1904179
Classe di rischio
9
Gruppo di imballaggio
III
Codice tariffe armonizzato
2930.90
TSCA
Yes
RTECS
DA6200000

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