Trimethylsulfoxonium iodide, 98+%, Thermo Scientific Chemicals
Thermo Scientific Chemicals
Trimethylsulfoxonium iodide, 98+%, Thermo Scientific Chemicals
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500 g
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100 g
Catalog number A14589.36
also known as A14589-36
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Chemical Identifiers
CAS1774-47-6
IUPAC Nametrimethyl(oxo)-λ⁶-sulfanylium iodide
Molecular FormulaC3H9IOS
InChI KeyBPLKQGGAXWRFOE-UHFFFAOYSA-M
SMILES[I-].C[S+](C)(C)=O
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)White to yellow
FormCrystals or crystalline powder
Assay (Titration ex Iodide)≥98.0 to ≤102.0%
Identification (FTIR)Conforms
Trimethylsulfoxonium iodide reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Trimethylsulfoxonium iodide reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.

Solubility
Soluble in water.

Notes
Incompatible with strong oxidizing agents and strong bases. Light sensitive.
RUO – Research Use Only

General References:

  1. The ylide, generated with strong base, is a methylene transfer reagent.
  2. For an example (conversion of cyclohexanone to the epoxide), see: Org. Synth. Coll., 5, 755 (1973). In contrast to Trimethyl sulfonium iodide, A12639, reaction with ɑß-unsaturated ketones occurs by 1,4-addition to give cyclopropanes: J. Am. Chem. Soc., 87, 1353 (1965):
  3. Efficient addition to enones has been effected with a highly basic system consisting of KOH in DMSO with a phase-transfer catalyst: Synth. Commun., 26, 1785 (1996).
  4. Reaction with epoxides gives oxetanes, unlike the sulfonium ylide which gives allylic alcohols: J. Org. Chem., 48, 5133 (1983); Synthesis, 1140 (1987); cf Tetrahedron Lett., 35, 5449 (1994):
  5. Similarly, N-arenesulfonylaziridines undergo ring expansion to azetidines with inversion at one carbon. Thus, cis-substituted aziridines give trans-azetidines and vice versa: Tetrahedron, 45, 1851 (1989):
  6. Review of the chemistry of sulfonium ylides: Russ. Chem. Rev., 50, 481 (1981). Extensive review of the synthetic applications of dimethylsulfoxonium methylide: Tetrahedron, 43, 2609 (1987).
  7. Sathishkumar, S.; Mahasampathgowri, S.; Balasubramanian, K. K.; Saiganesh, R. A convenient synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension. Tetrahedron Lett. 2015, 56 (26), 4031-4035.
  8. Kagawa, N.; Suzuki, M.; Kogure, N.; Toume, K. Characterization of organic iodides with iodine-127 nuclear magnetic resonance spectroscopy. Tetrahedron Lett. 2015, 56 (42), 5795-5798.