Trimethyltin hydroxide

Trimethyltin hydroxide
Names
IUPAC name
Trimethyltin hydroxide
Other names
  • Hydroxytrimethylstannane
  • Hydroxytrimethyltin
  • Trimethylstannanol
  • Trimethylstannyl hydroxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.202.818
EC Number
  • 677-697-9
UNII
  • InChI=1S/3CH3.H2O.Sn/h3*1H3;1H2;/q;;;;+1/p-1
    Key: OJZNYUDKNVNEMV-UHFFFAOYSA-M
  • O[Sn](C)(C)C
Properties
(CH3)3SnOH
Molar mass 180.822 g·mol−1
Appearance White crystalline solid[1][2]
Melting point 118 °C (244 °F; 391 K)[3] (sublimes)
Soluble[2]
Solubility Soluble in organic solvents[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic
GHS labelling:[4]
GHS06: ToxicGHS09: Environmental hazard
Danger
H300, H310, H330, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, P501
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 hydroxide is an organotin compound with the chemical formula (CH3)3SnOH. It is a white crystalline solid.

Synthesis

Trimethyltin hydroxide can be synthesized by reaction of trimethyltin chloride with a strong base in methanol.

(CH3)3SnCl + KOH → (CH3)3SnOH + KCl

It can also be synthesized by hydrolysis of trimethyltin chloride and purification by sublimation.[2]

Structure

Structure of solid trimethyltin hydroxide.

Solid trimethyltin hydroxide is a coordination polymer. It forms orthorhombic crystals.[5] The room temperature crystal structure of trimethyltin hydroxide comprises a total of 32 crystallographically independent (CH3)3SnOH units arranged in four independent coordination polymer strands.[6] Each strand is an infinite linear chain of (CH3)3SnOH units, where in each unit Sn is approximately trigonal bipyramidal, surrounded by three methyl groups at the equator and two hydroxyl groups at the poles, where oxygens are shared between the units. The hydroxide groups play role as bridges between the units.[5] Below 160 K (−113 °C; −172 °F) the crystal structure undergoes phase transition.[6]

Uses

Trimethyltin hydroxide is a reagent used for the cleavage of nonhindered alkyl esters. It is a method that is used for mild, efficient and selective hydrolysis of esters to produce corresponding carboxylic acids.[2][7] Trimethyltin hydroxide is used in the synthesis of modified thymines, which is useful as inhibitors of RNase A. It reacts with 2,2-disubstituted benzothiazolines to produce trialkyltin derivatives of sulfur containing Schiff base complexes.[1]

References

  1. 1 2 https://www.thermofisher.com/order/catalog/product/071167.06
  2. 1 2 3 4 5 Furlán, Ricardo L. E.; Mata, Ernesto G. (2011). "Trimethyltin Hydroxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01292. ISBN 978-0-471-93623-7.
  3. ↑ https://www.sigmaaldrich.com/GB/en/sds/aldrich/cds025240
  4. ↑ PubChem. "Stannane, hydroxytrimethyl-". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-20.
  5. 1 2 https://journals.iucr.org/a/issues/2005/a1/00/a33185/a33185.pdf
  6. 1 2 Anderson, Kirsty M.; Tallentire, Sarah E.; Probert, Michael R.; Goeta, Andrés E.; Mendis, Budhika G.; Steed, Jonathan W. (2011). "Trimethyltin Hydroxide: A Crystallographic and High Z ′ Curiosity". Crystal Growth & Design. 11 (3): 820–826. doi:10.1021/cg101464j.
  7. ↑ Nicolaou, K. C.; Estrada, Anthony A.; Zak, Mark; Lee, Sang Hyup; Safina, Brian S. (2005). "A Mild and Selective Method for the Hydrolysis of Esters with Trimethyltin Hydroxide". Angewandte Chemie International Edition. 44 (9): 1378–1382. doi:10.1002/anie.200462207. PMID 15674985.
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