Trimethyltin acetate

Trimethyltin acetate
Names
IUPAC name
Trimethylstannyl acetate[1]
Other names
  • Acetic acid trimethylstannyl ester[1]
  • Acetoxytrimethyltin[1]
  • Trimethyltin acetate[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.289.298
UNII
  • InChI=1S/C2H4O2.3CH3.Sn/c1-2(3)4;;;;/h1H3,(H,3,4);3*1H3;/q;;;;+1/p-1
    Key: XZVPFLCTEMAYFI-UHFFFAOYSA-M
  • CC(=O)O[Sn](C)(C)C
Properties
CH3COOSn(CH3)3
Molar mass 222.859 g·mol−1
Appearance White crystalline solid
Melting point 193 °C (379 °F; 466 K)[2]
Solubility Sparingly soluble in chloroform and carbon tetrachloride.
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic
GHS labelling:
Danger
Lethal dose or concentration (LD, LC):
9 mg/kg (rat, oral)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethyltin acetate is an organotin compound with the chemical formula CH3COOSn(CH3)3. It is a white crystalline solid. It is a poison.

Preparation

Trimethyltin acetate can be prepared by reaction between tetramethyltin and mercury(I) acetate in methanol at room temperature.[3]

2 (CH3)4Sn + (CH3COO)2Hg2 → 2 CH3COOSn(CH3)3 + (CH3)2Hg + Hg

The previously known insoluble trimethyltin acetate has been converted to a new, soluble form by heating in a sealed tube with cyclohexane at 100 °C. The effects of temperature, concentration, and added complexing agents on the infrared and NMR spectra are reported. The results show an equilibrium in solution between monomeric and polymeric forms. It is suggested that the polymeric forms may have a cyclic structure, in contrast to the infinite linear polymeric structure attributed to the insoluble form.[4]

Uses

Trimethyltin acetate shows low antifungal activity.[5]

Safety

Triorganyltin compounds, like trimethyltin acetate, are poisonous. They are highly toxic if swallowed and harmful in contact with skin. Cause serious skin and eye irritation. They can cause serious eye damage. Cause serious damages to organs and nerves. They are highly toxic to aquatic life, with long-lasting effects.[6][7]

References

  1. ^ a b c d "Trimethyltin acetate".
  2. ^ "CAS Common Chemistry".
  3. ^ Plazzogna, Gualtiero; Peruzzo, Valerio; Tagliavini, Giuseppe (1969). "A new method of preparing a soluble form of trimethyltin acetate". Journal of Organometallic Chemistry. 16 (3): 500–502. doi:10.1016/S0022-328X(00)89777-6. Retrieved 2026-01-05.
  4. ^ Simons, Paul B.; Graham, W. A. G. (June 1, 1967). "Studies of organotin chemistry: I. Preparation and properties of new, soluble forms of trimethyltin formate and acetate". Journal of Organometallic Chemistry. 8 (3): 479–490. doi:10.1016/S0022-328X(00)83669-4. ISSN 0022-328X.
  5. ^ van der Kerk, G. J. M.; Luijten, J. G. A. (1956). "Investigations on organo-tin compounds. V The preparation and antifungal properties of unsymmetrical tri-n-alkyltin acetates". Journal of Applied Chemistry. 6 (2): 56–60. doi:10.1002/jctb.5010060202. ISSN 1934-998X.
  6. ^ "DETOX Program Fact Sheet – Organotin Compounds" (PDF). REWE Group. Retrieved 3 March 2026.
  7. ^ Barbosa, Carolina Monteiro de Lemos; Ferrão, Fernanda Magalhães; Graceli, Jones B. (2018). "Organotin Compounds Toxicity: Focus on Kidney". Frontiers in Endocrinology. 9 256. doi:10.3389/fendo.2018.00256. PMC 5972511. PMID 29872423.
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