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HomeProduct name listTrimethylsulfoxonium iodide

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
Trimethylsulfoxonium iodide Structural

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)
ghs
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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