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.
Synthesis Trimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride.
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
Uses Trimethyltin chloride is used as a source of the trimethylstannyl group ((CH3)3Sn−). For example, it is a precursor to vinyltrimethylstannane ((CH3)3SnCH=CH2) and indenyltrimethylstanane (CH3)3SnC9H7 (see Transition metal indenyl complex):
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:
2 Na + 2 (CH3)3SnCl → (CH3)3Sn−Sn(CH3)3 + 2 NaCl
Toxicity The ototoxicity of trimethyltin chloride in humans is not conclusively known. In guinea pigs, administered intraperitoneally, it is acutely and persistently ototoxic at 2 mg/kg (mechanisms may include damage to hair cells and vasculature of the cochlea), but in rats no such effect occurred.
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