Trimethyltin chloride

Trimethyltin chloride

Ball-and-stick model of the trimethyltin chloride molecule
Names
Other names chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride
Identifiers
CAS Number	1066-45-1 Y
Properties
Chemical formula	C3H9SnCl
Molar mass	199.27 g/mol
Melting point	38.5 °C (101.3 °F; 311.6 K)
Boiling point	148 °C (298 °F; 421 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Trimethyltin chloride is an organotin compound with the formula (CH₃)₃SnCl. It is a white solid that is highly toxic and has a stench. It is susceptible to hydrolysis.

Synthesis

Trimethyltin chloride can be prepared by the redistribution 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 involves treating the corresponding hydroxide or oxide with a halogenating agent such as hydrogen chloride or thionyl chloride (SOCl₂):

Me₃SnOH + HCl → Me₃SnCl + H₂O

Uses

Trimethyltin chloride is used as a source of the trimethylstannyl group. For example, it is a precursor to vinyltrimethylstannane:

CH₂=CHMgBr + Me₃SnCl → Me₃SnCH=CH₂ + MgBrCl

An example of an organolithium 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 useful in organic synthesis, 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)