CAS · 1774-47-6
Product Overview
Trimethylsulfoxonium iodide is a high-purity pharmaceutical-intermediates supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance: | White to light yellow crystals |
|---|---|
| Assay: | 99.0% min |
| Loss on drying: | 0.20% max |
| Residue on ignition: | 0.20% max |
| Heavy metals: | 0.002% max |
Applications
1.1 Epoxidation Reagent (Core Use)
Trimethylsulfoxonium iodide is most widely used in organic synthesis for the epoxidation of carbonyl compounds.
When treated with strong base (commonly sodium hydride, NaH), it forms dimethyloxosulfonium methylide (DMSO ylide), a reactive intermediate that can transfer a methylene group to carbonyl compounds.
This results in epoxides, especially from aldehydes and ketones, in high yields with excellent regioselectivity and stereoselectivity.
1.2 Ylide Chemistry
As a sulfur ylide precursor, it's crucial in non-metal-catalyzed carbene transfer reactions.
Sulfur ylides generated from trimethylsulfoxonium iodide are used in:
Cyclopropanation
Epoxidation
Aziridination
These reactions are popular in asymmetric synthesis and pharmaceutical research.
1.3 Pharmaceutical and Fine Chemical Synthesis
Applied in the synthesis of drug intermediates, especially where epoxides are key structural motifs or reactive intermediates.
Widely adopted in medicinal chemistry workflows due to its compatibility with diverse functional groups.
1.4 Academic and Industrial Research
Frequently used in synthetic methodology development, natural product synthesis, and polymer modification.
The compound is favored in academic labs and chemical process development for its reliable performance in ylide-mediated transformations.
Benefits
2.1 High Reactivity Under Mild Conditions
Enables efficient epoxidation at ambient temperatures without the need for harsh oxidizing agents.
Safer and more selective than classical epoxidation reagents like peracids.
2.2 Clean Reaction Profiles
Produces minimal byproducts, often just DMSO and iodide salt, which are easy to remove.
Results in high-purity epoxides, which are important in pharmaceutical production.
2.3 Compatible with Diverse Substrates
Works well with a wide range of aldehydes, ketones, and α,β-unsaturated carbonyl compounds.
Tolerates many sensitive functional groups (e.g., esters, amides, nitro groups), making it versatile for complex molecule synthesis.
2.4 Reliable, Commercially Available Reagent
Stable under standard storage conditions and commercially available in various grades.
Easy to handle in both laboratory-scale and industrial processes.
Conclusion
Trimethylsulfoxonium iodide (CAS 1774-47-6) is a vital reagent in modern organic chemistry, best known for its role in generating sulfur ylides for selective epoxidation reactions. Its mild reactivity profile, functional group compatibility, and clean reaction outcomes make it a preferred choice in both research and industrial synthesis. As synthetic strategies evolve toward greener and more selective transformations, trimethylsulfoxonium iodide remains a cornerstone reagent for constructing epoxides and other valuable small-ring intermediates.
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