Trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide (CAS 1774-47-6) is a pale yellow crystalline powder with a molecular weight of 220.07 g/mol. This sulfur compound is primarily utilised in organic synthesis as a building block. Upon treatment with a strong base, it generates an ylide that is crucial for the formation of epoxides from aldehydes and ketones, and also for the synthesis of cyclopropyl esters from α,β-unsaturated esters. It is soluble in water, offering versatility in reaction conditions.
Epoxide Synthesis
Trimethylsulfoxonium iodide, upon deprotonation to form the corresponding ylide, reacts with aldehydes and ketones to yield epoxides. This is a fundamental transformation in organic chemistry for the creation of three-membered oxygen-containing rings.
Cyclopropane Ester Formation
The ylide derived from Trimethylsulfoxonium iodide can undergo conjugate addition to α,β-unsaturated esters. Subsequent cyclisation leads to the formation of cyclopropyl esters, providing a route to strained carbocyclic rings.
Organic Synthesis Building Block
As a sulfoxonium salt, this compound serves as a valuable building block in a wide array of organic syntheses. Its ability to generate a nucleophilic ylide makes it indispensable for carbon-carbon bond formation and functional group transformations.
| Molecular weight | 220.07 |
|---|---|
| Linear formula | (CH3)3S(I)O |
| Assay | 98% |
| Solubility | Soluble in water |
| Loss on drying | loss on drying 0.5 % Max. |
| Application | Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5 |
| Melting point | 208-212 °C (dec.)(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 2 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
| Description | Pale Yellow Crystalline Powder |
|---|
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Trimethylsulfoxonium iodide used for?
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Trimethylsulfoxonium iodide is used as a reagent in organic synthesis, primarily for the preparation of epoxides from carbonyl compounds and cyclopropyl esters from α,β-unsaturated esters, by generating a sulfoxonium ylide.
What is the CAS number and formula for Trimethylsulfoxonium iodide?
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The CAS number for Trimethylsulfoxonium iodide is 1774-47-6. Its linear formula is (CH3)3S(I)O.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Trimethylsulfoxonium iodide with an assay of 98%. This is typically considered a technical or research grade, and TSS does not represent it as USP, BP, or EP grade.
What are the safety and handling precautions for Trimethylsulfoxonium iodide?
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Trimethylsulfoxonium iodide is classified with GHS hazards, requiring appropriate safety measures. Personal protective equipment, including eyeshields, gloves, and a P1 (EN143) or N95 (US) respirator filter, should be used. It is classified as WGK 2 in Germany, indicating a moderate hazard to water.
How is Trimethylsulfoxonium iodide packed and shipped?
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Trimethylsulfoxonium iodide is carefully packed to ensure safe handling and transport. As a specialist global supplier, Tech Serve Solutions exports chemicals worldwide, adhering to all relevant shipping regulations.
How can I request a quote or sample for Trimethylsulfoxonium iodide?
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To request a quote or a sample of Trimethylsulfoxonium iodide, please contact the Tech Serve Solutions sales team via our website or direct inquiry channels.
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