Trimethyltin chloride

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Trimethyltin chloride
Trimethyltin chloride.png
Identifiers
CAS number 1066-45-1 YesY
Properties
Molecular formula C3H9SnCl
Molar mass 199.27 g/mol
Melting point 38.5 °C (311.65 K)[1]
Boiling point 148 °C (421.15 K)
Hazards
MSDS External MSDS
R-phrases 26/27/28-50/53
S-phrases 26-27-28-45-60-61
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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.

Synthesis[edit]

Trimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride.[2]

SnCl4 + 3 SnMe4 → 4 Me3SnCl

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):

Me3SnOH + HCl → Me3SnCl + H2O

Uses[edit]

Trimethyltin chloride is used as a source of the trimethylstannyl group.[3] For example, it is a precursor to vinyltrimethylstannane:

CH2=CHMgBr + Me3SnCl → Me3SnCH=CH2

An example of an organolithium 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, 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[edit]

  1. ^ Lide, D. R.; Milne, G. W. (1994). Handbook of Data on Organic Compounds 4 (3rd ed.). CRC Press. p. 4973. 
  2. ^ Scott, W. J.; Crisp, G. T.; Stille, J. K. (1990), Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-Butylcyclohexen-1-yl)-2-propen-1-one, Org. Synth. 68: 116 ; Coll. Vol. 8: 97 
  3. ^ Davies, A. G. (2008). "Tin Organometallics". Comprehensive Organometallic Chemistry 3. Elsevier. pp. 809–883. doi:10.1016/B0-08-045047-4/00054-6.