Trimethyltin chloride is an
organotin
Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...
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
In chemistry, redistribution usually refers to the exchange of anionic ligands bonded to metal and metalloid centers. The conversion does not involve redox
Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical ...
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 k ...
with
tin tetrachloride
Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound of tin and chlorine with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other ...
.
:
This redistribution reaction is typically performed with no solvent because high temperatures are required and purification is simplified.
A second route to involves treating the corresponding
hydroxide or oxide (in the following reaction, trimethyltin hydroxide ) with a halogenating agent such as
hydrogen chloride
The Chemical compound, compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hyd ...
or
thionyl chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagen ...
():
:
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 (see
Transition metal indenyl complex 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 ...
):
:
:
An example of an
organolithium
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...
reagent reacting with to form a
tin-carbon bond is:
:
Organotin compounds derived from are useful in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
, especially in
radical chain reactions. is a precursor to compounds used in
PVC
Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons o ...
stabilization.
Reduction of trimethyltin chloride with sodium gives hexamethylditin:
:
References
{{reflist
Chlorides
Metal halides
Organotin compounds
Foul-smelling chemicals
Tin(IV) compounds
Methyl compounds