Trimethyltin chloride
Encyclopedia
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
.
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):
Another example of a Grignard 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.
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 Edward Frankland in 1849...
compound]] with the formula (CH3)3SnCl. It is a white solid that is highly toxic and has a stench. It is susceptible to hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
.
Synthesis
Trimethyltin chloride can be prepared by the redistribution reactionRedistribution (chemistry)
In chemistry, redistribution usually refers to the exchange of anionic ligands bonded to metal and metalloid centers. The conversion does not involve redox, in contrast to disproportionation reactions. Redistribution reactions are usefully conducted at higher temperatures; upon cooling the...
of tetramethyltin
Tetramethyltin
Tetramethyltin is an organometallic compound with the formula 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 ketones...
with tin tetrachloride.
- SnCl4 + 3 SnMe4 → 4 Me3SnCl
This is the Kocheshkov redistribution reaction. It is performed under an inert atmosphere, such as argon
Argon
Argon is a chemical element represented by the symbol Ar. Argon has atomic number 18 and is the third element in group 18 of the periodic table . Argon is the third most common gas in the Earth's atmosphere, at 0.93%, making it more common than carbon dioxide...
, typically with no solvent.
A second route to Me3SnCl involves treating the corresponding hydroxide
Hydroxide
Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and a hydrogen atom held together by a covalent bond, and carrying a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, as a ligand, a nucleophile, and a...
or oxide with a halogenating agent such as hydrogen chloride
Hydrogen chloride
The compound hydrogen chloride has the formula HCl. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity. Hydrogen chloride gas and hydrochloric acid are important in technology and industry...
or thionyl chloride
Thionyl chloride
Thionyl chloride is an inorganic compound with the formula SOCl2. It is a reactive chemical reagent used in chlorination reactions. It is a colorless, distillable liquid at room temperature and pressure that decomposes above 140 °C. Thionyl chloride is sometimes confused with sulfuryl...
(SOCl2):
- Me3SnOH + HCl → Me3SnCl + H2O
Uses
Trimethyltin chloride is used as a source of the trimethylstanyl group. For example, it is a precursor to vinyltrimethylstannane:- CH2=CHMgBr + Me3SnCl → Me3SnCH=CH2
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 useful in organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
, especially in radical chain
Radical (chemistry)
Radicals are atoms, molecules, or ions with unpaired electrons on an open shell configuration. Free radicals may have positive, negative, or zero charge...
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)