Trimethyltin chloride
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| Trimethyltin chloride | |
|---|---|
 |
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| Other names | chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride |
| Identifiers | |
| CAS number | [1066-45-1] |
| 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, 100 kPa) Infobox disclaimer and references |
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Trimethyltin chloride ((CH3)3SnCl) is a moisture sensitive organotin compound having a strong unpleasant stench that is soluble in organic solvents, but hydrolyzes.
[edit] Synthesis
Trimethyltin chloride can be prepared by 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 is by reacting the related tin hydroxide or oxide with a halogenating agent like either HCl or SOCl2.
- Me3SnOH + SOCl2 → Me3SnCl + HSOCl +1/2O2
[edit] Uses
Timethyltin chloride is used with Grignard reagents to generate tin-carbon bonds. [3] An example is:
- CH2CHMgBr + Me3SnCl → Me3SnCHCH2
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 used extensively in organic syntheses, 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)
[edit] References
- ^ Lide, David R & Milne, G.W.A. Handbook of Data on Organic Compounds. 3rd Edition. Volume IV. CRC Press: 1994. pg 4973.
- ^ Scott, William J. Crisp, G. T., Stille, J. K. (1993). "Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-Butylcyclohexen-1-yl)-2-propen-1-one". Org. Synth.; Coll. Vol. 8: 97.
- ^ Davies, A.G. "Tin Organometallics". Comprehensive Organometallic Chemistry III. Elsevier B.V.: 2008. pg 809-883 doi:10.1016/B0-08-045047-4/00054-6
