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

A14846 Thioanisole, 99%

CAS Number
100-68-5
Synonyms
Methyl phenyl sulfide

Size Price ($) Quantity Availability
25g 20.07
100g 37.90
500g 132.87
2500g 474.81
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Thioanisole, 99%

MDL
MFCD00008559
EINECS
202-878-2

Chemical Properties

Formula
C7H8S
Formula Weight
124.21
Melting point
-15°
Boiling Point
188-189°
Flash Point
73°(163°F)
Density
1.058
Refractive Index
1.5860
Solubility
Miscible with most common organic solvents. Immiscible with water.

Applications

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.

Notes

Incompatible with strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: 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.

Precautionary Statements: 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.

Other References

Beilstein
1904179
Hazard Class
9
Packing Group
III
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
DA6200000

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