Trimethylsulfoxonium iodide
- CAS NO.:1774-47-6
- Empirical Formula: C3H9IOS
- Molecular Weight: 220.07
- MDL number: MFCD00011899
- EINECS: 217-204-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-01 18:09:03
What is Trimethylsulfoxonium iodide?
Chemical properties
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER
The Uses of Trimethylsulfoxonium iodide
Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides.
The Uses of Trimethylsulfoxonium iodide
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
The Uses of Trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.
Synthesis
Trimethylsulfoxonium iodide is commonly prepared by a reaction of Dimethyl Sulfoxide with ≈2.5 equiv of Iodomethane. After refluxing for 24 h at 80?°C, the reaction mixture is cooled, and the crude solid product is filtered and washed with acetone to give the trimethylsulfoxonium iodide. Iodomethane has to be handled in a fume hood because of its high volatility and toxicity. Excess MeI is used to ensure the completion of the reaction.
storage
The iodide and chloride salts are hygroscopic and must be stored in a cool, dry place. They are incompatible with strong oxidizing agents and strong bases. The iodide salt is sensitive to light and needs to be protected from light as much as possible.
Properties of Trimethylsulfoxonium iodide
Melting point: | 208-212 °C (dec.) (lit.) |
Density | 1.7074 (estimate) |
storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
solubility | H2O: 50 mg/mL, clear |
form | Crystalline Powder |
color | White to light yellow |
PH | pH(50g/l, 25℃) : 4.8~6.0 |
Water Solubility | 15 g/L (20 ºC) |
Sensitive | Light Sensitive |
BRN | 3595854 |
InChI | InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1 |
CAS DataBase Reference | 1774-47-6(CAS DataBase Reference) |
EPA Substance Registry System | Sulfoxonium, trimethyl-, iodide (1774-47-6) |
Safety information for Trimethylsulfoxonium iodide
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for Trimethylsulfoxonium iodide
InChIKey | BPLKQGGAXWRFOE-UHFFFAOYSA-M |
SMILES | [S+](=O)(C)(C)C.[I-] |
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