View source for Trimethyltin chloride

{{Chembox new
|  ImageFile=trimethyltin chloride.png
|  ImageSize=100px
|   OtherNames = chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride
| Section1 = {{Chembox Identifiers
|   CASNo = 1066-45-1
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>3</sub>H<sub>9</sub>SnCl
|   MolarMass = 199.27 g/mol
|   MeltingPt = 38.5 °C (311.65 K)<ref> Lide, David R & Milne, G.W.A. Handbook of Data on Organic Compounds. 3<sup>rd</sup> Edition. Volume IV. CRC Press: 1994. pg 4973. </ref>
|   BoilingPt = 148 °C (421.15 K)
  }}
| Section3 = {{Chembox Hazards
|   RPhrases = 26/27/28-50/53
|   SPhrases = 26-27-28-45-60-61
|   ExternalMSDS = [http://hazard.com/msds/f2/bkn/bknln.html External MSDS]
  }}
}}
{{CMG}}



'''Trimethyltin chloride''' ((CH<sub>3</sub>)<sub>3</sub>SnCl) is a moisture sensitive organotin compound having a strong unpleasant stench that is soluble in organic solvents, but [[hydrolysis|hydrolyzes]]. 

==Synthesis==
Trimethyltin chloride  can be prepared by reaction of [[tetramethyltin]] with [[tin tetrachloride]].<ref>{{OrgSynth | author = Scott, William J. Crisp, G. T., Stille, J. K. | title = Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-''tert''-Butylcyclohexen-1-yl)-2-propen-1-one | collvol = 8 | collvolpages = 97 | prep = cv8p0097 | year = 1993}}</ref>

:SnCl<sub>4</sub>  +  3 SnMe<sub>4</sub> →  4 Me<sub>3</sub>SnCl

This is the Kocheshkov redistribution reaction. It is performed under an inert atmosphere, such as [[argon]], typically with no solvent. 


A second route to Me<sub>3</sub>SnCl is by reacting the related [[tin hydroxide]] or oxide with a halogenating agent like either HCl or SOCl<sub>2</sub>.

:Me<sub>3</sub>SnOH + SOCl<sub>2</sub> → Me<sub>3</sub>SnCl + HSOCl +<sup>1</sup>/<sub>2</sub>O<sub>2</sub>

==Uses==
Timethyltin chloride is used with [[Grignard reagent|Grignard reagents]] to generate tin-carbon bonds. <ref> 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}}</ref> An example is: 

:CH<sub>2</sub>CHMgBr + Me<sub>3</sub>SnCl  →  Me<sub>3</sub>SnCHCH<sub>2</sub>  

Another example of a Grignard reagent reacting with Me<sub>3</sub>SnCl to form a tin-carbon bond is

:LiCH(SiMe<sub>3</sub>)(GeMe<sub>3</sub>) + Me<sub>3</sub>SnCl  →  Me<sub>3</sub>SnCH(SiMe<sub>3</sub>)(GeMe<sub>3</sub>) + LiCl

Organotin compounds derived from Me<sub>3</sub>SnCl are used extensively in organic syntheses, especially in [[Radical_%28chemistry%29| radical chain]] reactions. Me<sub>3</sub>SnCl is a precursor to compounds used in PVC stabilization. 
Reduction of trimethyltin chloride gives tin-tin bonds. 
:Me<sub>3</sub>SnM + Me<sub>3</sub>SnCl  →  Sn<sub>2</sub>Me<sub>6</sub> + MCl (M = metal)

==References==
<references/>
[[Category:Organometallic compounds]]
[[Category:Tin compounds]]
[[Category:Chlorides]]
[[Category:Tin compounds]]
[[Category:Metal halides]]

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