Trimethyltin chloride
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| Names | |||
|---|---|---|---|
| Other names
chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride | |||
| Identifiers | |||
1066-45-1  | |||
| 3D model (Jmol) | Interactive image | ||
| ChemSpider | 13398 | ||
| ECHA InfoCard | 100.012.653 | ||
| PubChem | 14016 | ||
| UNII | 9E3BCA3684 | ||
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| Properties | |||
| C3H9SnCl | |||
| Molar mass | 199.27 g/mol | ||
| Melting point | 38.5 °C (101.3 °F; 311.6 K)[1] | ||
| Boiling point | 148 °C (298 °F; 421 K) | ||
| Hazards | |||
| Safety data sheet | External MSDS | ||
| R-phrases | 26/27/28-50/53 | ||
| S-phrases | 26-27-28-45-60-61 | ||
| Except where otherwise noted, 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
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
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 + MgBrCl
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
- ↑ Lide, D. R.; Milne, G. W. (1994). Handbook of Data on Organic Compounds. 4 (3rd ed.). CRC Press. p. 4973.
- ↑ 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, p. 97
- ↑ Davies, A. G. (2008). "Tin Organometallics". Comprehensive Organometallic Chemistry. 3. Elsevier. pp. 809–883. doi:10.1016/B0-08-045047-4/00054-6.