Trimethyltin chloride

Trimethyltin chloride
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 ;
	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R-phrases (outdated)	26/27/28-50/53
S-phrases (outdated)	26-27-28-45-60-61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. ; 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.
↑ Robert J. Morris, Scott L. Shaw, Jesse M. Jefferis, James J. Storhoff, Dean M. Goedde. "Monoindenyltrichloride Complexes of Titanium(IV), Zirconium(IV), and Hafnium(IV)". Inorg. Synth. 32: 215–221. doi:10.1002/9780470132630.ch36.

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[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. ; 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.

[4] Robert J. Morris, Scott L. Shaw, Jesse M. Jefferis, James J. Storhoff, Dean M. Goedde. "Monoindenyltrichloride Complexes of Titanium(IV), Zirconium(IV), and Hafnium(IV)". Inorg. Synth. 32: 215–221. doi:10.1002/9780470132630.ch36.