Trimethyltin chloride

Trimethyltin chloride
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
Y chloride (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 trimethylstanyl group.^[3] For example, it is a precursor to vinyltrimethylstannane:

CH₂=CHMgBr + Me₃SnCl → Me₃SnCH=CH₂

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 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

1. ^ Lide, David R & Milne, G.W.A. Handbook of Data on Organic Compounds. 3^rd Edition. Volume IV. CRC Press: 1994. pg 4973.
2. ^ 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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0097 ; Coll. Vol. 8: 97 
3. ^ 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