Trimethyltin chloride

Template:Chembox new Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Trimethyltin chloride ((CH₃)₃SnCl) is a moisture sensitive organotin compound having a strong unpleasant stench that is soluble in organic solvents, but hydrolyzes.

Synthesis

Trimethyltin chloride can be prepared by reaction of tetramethyltin with tin tetrachloride.

SnCl₄ + 3 SnMe₄ → 4 Me₃SnCl

This is the Kocheshkov redistribution reaction. It is performed under an inert atmosphere, such as argon, typically with no solvent.

A second route to Me₃SnCl is by reacting the related tin hydroxide or oxide with a halogenating agent like either HCl or SOCl₂.

Me₃SnOH + SOCl₂ → Me₃SnCl + HSOCl +¹/₂O₂

Uses

Timethyltin chloride is used with Grignard reagents to generate tin-carbon bonds. An example is:

CH₂CHMgBr + Me₃SnCl → Me₃SnCHCH₂

Another example of a Grignard reagent reacting with Me₃SnCl to form a tin-carbon bond is

LiCH(SiMe₃)(GeMe₃) + Me₃SnCl → Me₃SnCH(SiMe₃)(GeMe₃) + LiCl

Organotin compounds derived from Me₃SnCl are used extensively in organic syntheses, especially in radical chain reactions. Me₃SnCl is a precursor to compounds used in PVC stabilization. Reduction of trimethyltin chloride gives tin-tin bonds.

Me₃SnM + Me₃SnCl → Sn₂Me₆ + MCl (M = metal)

References

Template:WikiDoc Sources