Trimethyltin chloride

Trimethyltin chloride
Skeletal formula of trimethyltin chloride	Ball-and-stick model of the trimethyltin chloride molecule
Names
	Other names chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride
Identifiers
CAS Number	1066-45-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	13398 ;
ECHA InfoCard	100.012.653
PubChem CID	14016;
UNII	9E3BCA3684 ;
CompTox Dashboard (EPA)	DTXSID6042496 ;
	InChI InChI=1S/3CH3.ClH.Sn/h31H3;1H;/q;;;;+1/p-1 Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M ; InChI=1/3CH3.ClH.Sn/h31H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3 Key: KWTSZCJMWHGPOS-KMTPXCBSAM;
	SMILES C[Sn](C)(C)Cl;
Properties
Chemical formula	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R-phrases (outdated)	26/27/28-50/53
S-phrases (outdated)	26-27-28-45-60-61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).
	verify (what is ?)
	Infobox references

Trimethyltin chloride is an organotin compound with the formula (CH₃)₃SnCl. It is a white solid that is highly toxic and malodorous. 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 and indenyltrimethylstanane:[4]

CH₂=CHMgBr + Me₃SnCl → Me₃SnCH=CH₂ + MgBrCl

LiC₉H₇ + Me₃SnCl → Me₃SnC₉H₇ + LiCl

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". Organic Syntheses. 68: 116.CS1 maint: multiple names: authors list (link); Collective Volume, 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. ISBN 9780080450476.
Robert J. Morris, Scott L. Shaw, Jesse M. Jefferis, James J. Storhoff, Dean M. Goedde (2007). "Monoindenyltrichloride Complexes of Titanium(IV), Zirconium(IV), and Hafnium(IV)". Inorganic Syntheses. Inorg. Synth. Inorganic Syntheses. 32. pp. 215–221. doi:10.1002/9780470132630.ch36. ISBN 9780470132630.CS1 maint: uses authors parameter (link)

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Lide, D. R.; Milne, G. W. (1994). Handbook of Data on Organic Compounds. 4 (3rd ed.). CRC Press. p. 4973.

[2] 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". Organic Syntheses. 68: 116.CS1 maint: multiple names: authors list (link); Collective Volume, 8, p. 97

[3] Davies, A. G. (2008). "Tin Organometallics". Comprehensive Organometallic Chemistry. 3. Elsevier. pp. 809–883. doi:10.1016/B0-08-045047-4/00054-6. ISBN 9780080450476.

[4] Robert J. Morris, Scott L. Shaw, Jesse M. Jefferis, James J. Storhoff, Dean M. Goedde (2007). "Monoindenyltrichloride Complexes of Titanium(IV), Zirconium(IV), and Hafnium(IV)". Inorganic Syntheses. Inorg. Synth. Inorganic Syntheses. 32. pp. 215–221. doi:10.1002/9780470132630.ch36. ISBN 9780470132630.CS1 maint: uses authors parameter (link)