Trimethylsulfoxonium iodide Chemical Properties

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

InChIKey

BPLKQGGAXWRFOE-UHFFFAOYSA-M

SMILES

[S+](=O)(C)(C)C.[I-]

CAS DataBase Reference

1774-47-6(CAS DataBase Reference)

EPA Substance Registry System

Sulfoxonium, trimethyl-, iodide (1774-47-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36-24/25

WGK Germany 

2

RTECS 

WS3585000

F 

8

TSCA 

Yes

HS Code 

29309070

MSDS

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Trimethylsulfoxonium iodide Usage And Synthesis

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

Uses

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

Uses

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.

Uses

Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of 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.

Trimethylsulfoxonium iodide(1774-47-6)Related Product Information

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