Trimethyltin chloride

Names

Other names

chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride

Identifiers

CAS Number

1066-45-1^Y

3D model (Jmol)

9E3BCA3684^Y

InChI=1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1

Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M
InChI=1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3

Key: KWTSZCJMWHGPOS-KMTPXCBSAM

SMILES

C[Sn](C)(C)Cl

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)

Hazards

26/27/28-50/53

26-27-28-45-60-61

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

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.

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

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):

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

An example of an organolithium reagent reacting with Me₃SnCl to form a tin-carbon bond is:

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.

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