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A14846 Thioanisole, 99%

CAS Number
100-68-5
Synonyms
Methyl phenyl sulfide

Stock No. Size Price ($) Quantity Availability
A14846-14 25g 23.50
A14846-22 100g 40.10
A14846-36 500g 141.00
A14846-0E 2500g 579.00
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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
Storage & Sensitivity
Ambient temperatures.
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: H227-H302-H315-H317-H319

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

Precautionary Statements: P210-P261-P264b-P270-P272-P280-P301+P312-P302+P352-P305+P351+P338-P330-P333+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

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

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