| Identification | Back Directory | [Name]
Bis(methylthio)(trimethylstannyl)methane | [CAS]
62762-48-5 | [Synonyms]
Bis(methylthio)(trimethylstannyl)methane
Stannane, [bis(methylthio)methyl]trimethyl- | [Molecular Formula]
C6H16S2Sn | [MDL Number]
MFCD17013464 | [MOL File]
62762-48-5.mol | [Molecular Weight]
271.03 |
| Hazard Information | Back Directory | [Uses]
Bis(methylthio)(trimethylstannyl)methane is used as a precursor to acyl anion equivalent with 1,4-addition selectivity; dianion equivalent.
| [Synthesis Reference(s)]
[1]Bürstinghaus, R.; Seebach, D. CB 1977, 110, 841 (CA 1977, 87, 6118n).
[2] Seebach, D.; Kolb, M.; Gr?bel, B.-T. CB 1973, 106, 2277 (CA 1974, 80, 27 320t).
| [Synthesis]
Commercially available bis(methylthio)methane is deprotonated by n-Butyllithium in THF/hexane at -60 to 0 °C. The resulting lithio derivative is quenched at -40 °C with 1 equiv of Chlorotrimethylstannane. An aqueous workup followed by vacuum distillation affords the bis(methylthio)(trimethylstannyl)methane reagent in 82% yield.[1] The analogous Bis(methylthio)(trimethylsilyl)methane can be prepared by a similar procedure.[2]
| [Precautions]
Bis(methylthio)(trimethylstannyl)methane should be considered toxic and should be handled with appropriate care. Use in a fume hood. |
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