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Trimethyltin chloride
Chemical compound From Wikipedia, the free encyclopedia
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Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.
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Synthesis
Trimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride.[3]
- SnCl4 + 3 Sn(CH3)4 → 4 (CH3)3SnCl
This redistribution reaction is typically performed with no solvent because high temperatures are required and purification is simplified.
A second route to (CH3)3SnCl involves treating the corresponding hydroxide or oxide (in the following reaction, trimethyltin hydroxide (CH3)3SnOH) with a halogenating agent such as hydrogen chloride or thionyl chloride (SOCl2):
- (CH3)3SnOH + HCl → (CH3)3SnCl + H2O
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Uses
Trimethyltin chloride is used as a source of the trimethylstannyl group ((CH3)3Sn−).[4] For example, it is a precursor to vinyltrimethylstannane ((CH3)3SnCH=CH2)[5] and indenyltrimethylstanane (CH3)3SnC9H7 (see Transition metal indenyl complex):[6]
- CH2=CHMgBr + (CH3)3SnCl → (CH3)3SnCH=CH2 + MgBrCl
- LiC9H7 + (CH3)3SnCl → (CH3)3SnC9H7 + LiCl
An example of an organolithium reagent reacting with (CH3)3SnCl to form a tin-carbon bond is:
- LiCH(Si(CH3)3)(Ge(CH3)3) + (CH3)3SnCl → (CH3)3SnCH(Si(CH3)3)(Ge(CH3)3) + LiCl
Organotin compounds derived from Me3SnCl are useful in organic synthesis, especially in radical chain reactions. (CH3)3SnCl is a precursor to compounds used in PVC stabilization. Reduction of trimethyltin chloride with sodium gives hexamethylditin:[7]
- 2 Na + 2 (CH3)3SnCl → (CH3)3Sn−Sn(CH3)3 + 2 NaCl
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References
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