Tetramethyltin
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| Tetramethyltin | |
|---|---|
| |
| IUPAC name | tetramethyltin |
| Other names | Tin tetramethyl tetramethylstannane |
| Identifiers | |
| CAS number | |
| Properties | |
| Molecular formula | C4H12Sn |
| Molar mass | 178.85 g/mol |
| Appearance | colorless liquid |
| Density | 1.291 g/cm3 |
| Melting point |
-54 °C (219 K) |
| Boiling point |
74-75 °C (347-348 K) |
| Hazards | |
| R-phrases | R26/27/28, R50/53 |
| S-phrases | S26, S27, S28, S45, S60, S61 |
| 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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Tetramethyltin is an organometallic compound with the formula (CH3)4Sn. This liquid, one of the simplest organotin compounds, is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones.
Synthesis and structure
Tetramethyltin is synthesized by reaction of the Grignard reagent methylmagnesium iodide, with SnCl4, [1] which is synthesized by reacting tin metal with chlorine gas.[1]
- 4 CH3MgI + SnCl4 → (CH3)4Sn + 4 MgICl
In tetramethyltin, the metal surrounded by four methyl groups in a tetrahedral structure is a heavy analogue of neopentane.
Applications
Precursor to methyltin compounds
Tetramethyltin is a precursor to trimethyltin chloride (and related methyltin halides), which are precursors to orther organotin compounds. These methyltin chlorides are prepared via the so-called Kocheshkov redistribution reaction. Thus, SnMe4 and SnCl4 are allowed to react at temperatures between 100 °C and 200 °C to give Me3SnCl as a product:
- SnCl4 + 3 SnMe4 → 4 Me3SnCl
A second route to trimethyltin chloride utilizing tetramethyltin involves the reaction of mercury (II) chloride to react with SnMe4.[1]
- 4 HgCl2 + 4 SnMe4 → 4 Me3SnCl + 4 MeHgCl
A variety of methyltin compounds are used as precursors for stabilizers in PVC. Di- and trimercapto tin compounds are used to inhibit the dehydrochlorination, which is the pathway for photolytic and thermal degradation of PVC.[1]
Surface functionalization
Tetramethyltin decomposes in the gas phase at about 277 °C (550 K) Me4Sn vapor reacts with silica to give Me3Sn-grafted solid.
- Me4Sn + ≡SiOH → ≡SiOSnMe3 + MeH
This reaction is also possible with other alkyl substituents. In a similar process, tetramethyltin has been used to functionalize certain zeolites at temperatures as low as -90 °C.[1]
Applications in organic synthesis
In organic synthesis, tetramethyltin undergoes palladium-catalyzed coupling reactions with acid chlorides to give methyl ketones:[1]
- SnMe4 + RCOCl → RCOMe + Me3SnCl
References
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
