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33577-16-1 - Methyl (methylthio)methyl sulfoxide, 97% - Formaldehyde dimethyl thioacetal monoxide - Methyl (methylsulfinyl)methyl sulfide - L00510 - Alfa Aesar

L00510 Methyl (methylthio)methyl sulfoxide, 97%

CAS Number
33577-16-1
Synonyms
Formaldehyde dimethyl thioacetal monoxide
Methyl (methylsulfinyl)methyl sulfide

Size Price ($) Quantity Availability
10g 50.40
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Methyl (methylthio)methyl sulfoxide, 97%

MDL
MFCD00002091
EINECS
251-577-2

Chemical Properties

Formula
C3H8OS2
Formula Weight
124.22
Boiling Point
222-226°
Flash Point
>110°(230°F)
Density
1.222
Refractive Index
1.5520
Sensitivity
Hygroscopic

Literature References

Readily undergoes metallation with NaH, n-BuLi, etc. to give a useful formaldehyde anion synthon. Products are readily hydrolyzed by acid.

/n

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):

/n

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).

/n

Other References

Beilstein
906789
Harmonized Tariff Code
2930.90
TSCA
Yes

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