Tetramethyltin: Difference between revisions

| verifiedrevid = 300526473

| ImageFile = Tetramethyltin.png

| ImageFile_Ref = {{Chemboximage|correct|??}}

| ImageSize = 121

| ImageName = Stereo structural formula of tetramethyltin

| IUPACName = Tetramethyltin

| SytematicName = <!-- Tetramethylstannane (substitutive) OR Tetramethyltin (additive) -->

| OtherNames = Tin tetramethyl<br />

| Section1 = {{Chembox Identifiers

| CASNo = 594-27-4

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 11661

| PubChem_Ref = {{Pubchemcite|correct|PubChem}}

| ChemSpiderID = 11171

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 209-833-6

| UNNumber = 3384

| ChEBI = 30420

| RTECS = WH8630000

| Beilstein = 3647887

| Gmelin = 1938

| SMILES = C[Sn](C)(C)C

| StdInChI = 1S/4CH3.Sn/h4*1H3;

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VXKWYPOMXBVZSJ-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}}}

| Section2 = {{Chembox Properties

| C = 4

| H = 12

| Sn = 1

| ExactMass = 179.996096955 g mol^-1

| Appearance = Colorless liquid

| Density = 1.291 g cm^-3

| MeltingPtC = -54

| BoilingPtCL = 74

| BoilingPtCH = 76}}

| Section3 = {{Chembox Hazards

| EUClass = {{Hazchem T+}}{{Hazchem N}}

| RPhrases = {{R26/27/28}}, {{R50/53}}

| SPhrases = {{S26}}, {{S27}}, {{S28}}, {{S45}}, {{S60}}, {{S61}}

| NFPA-H = 3

| NFPA-F = 4

| NFPA-R = 1

| FlashPt = -12 °C}}

| Section4 = {{Chembox Related

| Function = tetraalkylstannanes

| OtherFunctn = [[Tetrabutyltin]]<br />

[[Tetraethyltin]]

| OtherCpds = [[Neopentane]]<br />

[[Tetramethylsilane]]}}

Tetramethyltin is synthesized by reaction of the Grignard reagent methylmagnesium iodide, with SnCl₄, <ref name=Scott> {{cite journal

| author = Scott, W. J.; Jones, J. H.; Moretto, A. F.

| title = Tetramethylstannane

| journal = Encyclopedia of Reagents for Organic Synthesis

| date = 2002

| doi = 10.1002/047084289X.rt070}} </ref> which is synthesized by reacting tin metal with chlorine gas.<ref name=Thoonen>{{cite journal

| author = Thoonen, S. H. L.; Deelman, B.; van Koten, G; | title = Synthetic Aspects of Tetraorganotins and Organotin(IV) Halides

| journal = [[Journal of Organometallic Chemistry]]

| volume =689

| date = 2004

| pages = 2145&ndash;2157

| doi = 10.1016/j.jorganchem.2004.03.027

| issue = 13}}</ref>

In tetramethyltin, the metal surrounded by four methyl groups in a tetrahedral structure is a heavy analogue of [[neopentane]].

Tetramethyltin is a precursor to [[trimethyltin chloride]] (and related methyltin halides), which are precursors to other 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.<ref name=Scott/>

:4 HgCl₂ + 4 SnMe₄ → 4 Me₃SnCl + 4 MeHgCl

A variety of methyltin compounds are used as precursors for stabilizers in [[Polyvinylchloride|PVC]]. Di- and trimercapto tin compounds are used to inhibit the dehydrochlorination, which is the pathway for photolytic and thermal degradation of PVC.<ref name=Thoonen/>

Tetramethyltin decomposes in the gas phase at about 277 °C (550 K) Me₄Sn vapor reacts with silica to give Me₃Sn-grafted solid.

:Me₄Sn + &equiv;SiOH → &equiv;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.<ref>{{cite book | author = Davies, A. G. | chapter = Tin Organometallics | editor = Robert H. Crabtree and D. Michael P. Mingos | title = Comprehensive Organometallic Chemistry III | publisher = Elsevier | year = 2008.| pages = 809–883 | doi = 10.1016/B0-08-045047-4/00054-6}}</ref>

In [[organic synthesis]], tetramethyltin undergoes [[palladium-catalyzed coupling reactions]] with acid chlorides to give methyl ketones:<ref>{{cite journal | author = Labadie, J. and Stille, J. | title =Mechanisms of the palladium-catalyzed couplings of acid chlorides with organotin reagents | journal = [[J. Am. Chem. Soc.]] | volume = 105 | issue = 19 | pages = 6129 | year = 1983 | doi = 10.1021/ja00357a026}}</ref>

<references/>