Methyl (methylthio)methyl sulfoxide

• Catalog No.: L00510
• CAS Number: 33577-16-1
• M. F.: C3H8OS2
• M. W.: 124.22502
• Purity: 97%

SYNONYMS

• Title: (甲基硫代)甲基亚砜甲酯
• IUPAC name: methanesulfinyl(methylsulfanyl)methane
• IUPAC Traditional name: methanesulfinyl(methylsulfanyl)methane
• Synonyms: Methyl (methylsulfinyl)methyl sulfide; Formaldehyde dimethyl thioacetal monoxide

DATABASE IDS

• Beilstein Number: 906789
• MDL Number: MFCD00002091
• CAS Number: 33577-16-1
• EC Number: 251-577-2

PROPERTIES

• Purity: 97%
• Boiling Point: 222-226°C
• Density: 1.222
• Flash Point: >110°C(230°F)
• Refractive Index: 1.5520
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• Readily undergoes metallation with NaH, n-BuLi, etc. to give a useful formaldehyde anion synthon. Products are readily hydrolyzed by acid.
• Monoalkylation with alkyl halides: Tetrahedron Lett., 3151 (1971), or terminal epoxides leads to the homologated aldehydes: J. Org. Chem., 39, 3645 (1974). Dialkylation with alkyl halides affords, after hydrolysis, symmetrical ketones: Synthesis, 117 (1974). This reaction has also been applied to the synthesis of cyclobutanones and other cycloalkanones: Tetrahedron Lett., 3653 (1974); 2767 (1975). A Knoevenagel reaction with aryl aldehydes gives the ketene thioacetal monosulfoxide, readily solvolyzed in alcoholic HCl to an arylacetic ester: Tetrahedron Lett., 1383 (1972):
  
• With ketones, the lithio-derivative gives, after hydrolysis, ɑ-hydroxy aldehydes, not readily available by other routes: Tetrahedron Lett., 2681 (1972). Elimination from the intermediate adduct has also been used as a route to substituted acetic acids: Synthesis, 880 (1979).