Thioanisole

• Catalog No.: A14846
• CAS Number: 100-68-5
• M. F.: C7H8S
• M. W.: 124.20342
• Purity: 99%

SYNONYMS

• Title: 苯甲硫醚
• IUPAC name: (methylsulfanyl)benzene
• IUPAC Traditional name: thioanisole
• Synonyms: Methyl phenyl sulfide

DATABASE IDS

• Beilstein Number: 1904179
• CAS Number: 100-68-5
• MDL Number: MFCD00008559
• EC Number: 202-878-2

PROPERTIES

• Purity: 99%
• Boiling Point: 188-189°C
• Density: 1.058
• Flash Point: 57°C(135°F)
• Melting Point: -15°C
• Refractive Index: 1.5860
• GHS Hazard statements: H226-H302-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P280F
• Risk Statements: 22-36/37/38
• RTECS: DA6200000
• Safety Statements: 26-36/37
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: III

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).