Trimethyltin chloride

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)