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

A14846 Thioanisole, 99%

Número CAS
100-68-5
Nombre Alternativo
Methyl phenyl sulfide

Tamaño Precio ($) Cantidad Disponibilidad
25g 20,07
100g 37,90
500g 132,87
2500g 474,81
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Thioanisole, 99%

MDL
MFCD00008559
EINECS
202-878-2

Propiedades químicas

Fórmula
C7H8S
Peso molecular
124.21
Punto de fusión
-15°
Punto de ebullición
188-189°
Punto de inflamabilidad
73°(163°F)
Densidad
1.058
Índice de refracción
1.5860
Solubilidad
Miscible with most common organic solvents. Immiscible with water.

Aplicaciones

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.

Notas

Incompatible with strong oxidizing agents.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H315-H319-H317-H227-H411

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. Combustible liquid. Toxic to aquatic life with long lasting effects.

Indicaciones de precaución: P210-P261-P273-P280f-P305+P351+P338-P362-P301+P312-P363-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
1904179
Clase de peligro
9
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2930.90
TSCA
Yes
RTECS
DA6200000

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