Trimethyltin chloride is an

organotin Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered by ...

compound with the formula . It is a white solid that is highly toxic and malodorous. It is susceptible to

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

Synthesis

Trimethyltin chloride can be prepared by the redistribution reaction of

tetramethyltin Tetramethyltin is an organometallic compound with the formula (CH3)4Sn. This liquid, one of the simplest organotin compounds, is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ke ...

with

tin tetrachloride Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound with the formula Sn Cl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. I ...

. : This is the Kocheshkov redistribution reaction. It is performed under an inert atmosphere, such as

argon Argon is a chemical element with the symbol Ar and atomic number 18. It is in group 18 of the periodic table and is a noble gas. Argon is the third-most abundant gas in Earth's atmosphere, at 0.934% (9340 ppmv). It is more than twice as abu ...

, typically with no solvent. A second route to involves treating the corresponding hydroxide or oxide with a halogenating agent such as

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...

(): :

Uses

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

indenyl In organometallic chemistry, a transition metal indenyl complex is a coordination compound that contains one or more indenyl ligands. The indenyl ligand is formally the anion derived from deprotonation of indene. The η5-indenyl ligand is related ...

trimethylstanane: :CH₂=CHMgBr + Me₃SnCl → Me₃SnCH=CH₂ + MgBrCl :LiC₉H₇ + Me₃SnCl → Me₃SnC₉H₇ + LiCl An example of an

organolithium In organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, ...

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 Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

, 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

{{reflist Chlorides Metal halides Organotin compounds Foul-smelling chemicals Tin(IV) compounds Methyl complexes