Trimethyltin chloride

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.

Trimethyltin chloride
Skeletal formula of trimethyltin chloride
Ball-and-stick model of the trimethyltin chloride molecule
Names
Preferred IUPAC name
Chlorotri(methyl)stannane
Other names
chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.653 Edit this at Wikidata
UNII
  • InChI=1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1 ☒N
    Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M ☒N
  • InChI=1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3
    Key: KWTSZCJMWHGPOS-KMTPXCBSAM
  • C[Sn](C)(C)Cl
Properties
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R-phrases (outdated) 26/27/28-50/53
S-phrases (outdated) 26-27-28-45-60-61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).
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Infobox references

SynthesisEdit

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

UsesEdit

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)

ReferencesEdit

  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)