(methylsulfanyl)benzene

• ChemBase ID: 82195
• Molecular Formular: C7H8S
• Molecular Mass: 124.20342
• Monoisotopic Mass: 124.03467126
• SMILES: S(c1ccccc1)C
• Canonical SMILES: CSc1ccccc1
• InChI: InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
• InChIKey: HNKJADCVZUBCPG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (methylsulfanyl)benzene
• IUPAC Traditional name: thioanisole
• Synonyms: Thioanisole 99%; Thioanisole; Methyl phenyl sulfide; Methyl phenyl sulfide; THIOANISOLE; METHYL PHENYL SULFIDE; 茴香硫醚; 甲基苯基硫醚; 茴香硫醚; 甲基苯基硫醚; 苯甲硫醚

Database IDs

• CAS Number: 100-68-5
• EC Number: 202-878-2
• MDL Number: MFCD00008559
• Beilstein Number: 1904179
• PubChem SID: 24900081; 24889102; 24901909; 162069314
• PubChem CID: 7520
• FEMA ID: 3873
• Flavis Number: 12.162

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.6014628
• LogD (pH = 7.4): 2.6014628
• Log P: 2.6014628
• Molar Refractivity: 38.8169 cm^3
• Polarizability: 15.254656 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -15 °C(lit.); -15°C; -15°C
• Boiling Point: 188 °C(lit.); 188°C; 188-189°C
• Flash Point: 156.2 °F; 57°C(135°F); 69 °C
• Density: 1.057 g/mL at 20 °C(lit.); 1.058
• Refractive Index: 1.5860; 1.5865; n20/D 1.587; n20/D 1.587(lit.)

Safety Information

• Storage Warning: Harmful/Stench
• RTECS: DA6200000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: III
• Risk Statements: 22-36/37/38; R:22
• Safety Statements: 26; 26-36/37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H302-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P280F; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥99%; ≥99.0% (GC); 99%
• Grade: NI; purum; ReagentPlus®
• Linear Formula: C6H5SCH3

DETAILS

MP Biomedicals - 05216031

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 88470

Other Notes
Efficient promotor for the acid catalyzed cleavage of N-Z, O-benzyl and O-methyl protecting groups1,2,3

Sigma Aldrich - T28002

Packaging
25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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).