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.[1]
- 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. [2] 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:OrgSynth
- ↑ Davies, A.G. "Tin Organometallics". Comprehensive Organometallic Chemistry III. Elsevier B.V.: 2008. pg 809-883 doi:10.1016/B0-08-045047-4/00054-6