ChemicalBook > CAS DataBase List > Trimethylsulfoxonium iodide

Trimethylsulfoxonium iodide

Product Name
Trimethylsulfoxonium iodide
CAS No.
1774-47-6
Chemical Name
Trimethylsulfoxonium iodide
Synonyms
TMSOI;Trimethylsulfoxonium;TRIMETHYLSULPHOXONIUM IODIDE;Trimethyl sulfoxide iodide;trimethyloxosulphonium iodide;TriMethyloxosulfoniuM Iodide;NSC 71213;foxonium iodide;Trimethyl sulfoxide;RARECHEM AQ A1 0066
CBNumber
CB5304873
Molecular Formula
C3H9IOS
Formula Weight
220.07
MOL File
1774-47-6.mol
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Trimethylsulfoxonium iodide Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T80500
Product name
Trimethylsulfoxonium iodide
Purity
98%
Packaging
25g
Price
$59.47
Updated
2025/07/31
Sigma-Aldrich
Product number
T80500
Product name
Trimethylsulfoxonium iodide
Purity
98%
Packaging
100g
Price
$80.18
Updated
2025/07/31
TCI Chemical
Product number
T1065
Product name
Trimethylsulfoxonium Iodide
Purity
>98.0%(T)
Packaging
25g
Price
$22
Updated
2025/07/31
TCI Chemical
Product number
T1065
Product name
Trimethylsulfoxonium Iodide
Purity
>98.0%(T)
Packaging
100g
Price
$60
Updated
2025/07/31
Sigma-Aldrich
Product number
T80500
Product name
Trimethylsulfoxonium iodide
Purity
98%
Packaging
500g
Price
$149
Updated
2025/07/31
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Trimethylsulfoxonium iodide Chemical Properties,Usage,Production

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.

References

[1] Synthesis (Germany), 2017, vol. 49, # 12, p. 2652 - 2662
[2] Patent: EP2570410, 2013, A1. Location in patent: Paragraph 0064
[3] Patent: US2013/231369, 2013, A1. Location in patent: Paragraph 0102
[4] Journal of the Chemical Society [Section] C: Organic, 1971, p. 414 - 424
[5] Tetrahedron, 1958, vol. 3, p. 317

Trimethylsulfoxonium iodide Preparation Products And Raw materials

Raw materials

Preparation Products

1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE
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Trimethylsulfoxonium iodide Suppliers

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View Lastest Price from Trimethylsulfoxonium iodide manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Trimethylsulfoxonium iodide 1774-47-6
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-02-09
Hebei Chuanghai Biotechnology Co., Ltd
Product
Trimethylsulfoxonium iodide 1774-47-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-05
HebeiShuoshengImportandExportco.,Ltd
Product
Trimethylsulfoxonium iodide 1774-47-6
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-02

1774-47-6, Trimethylsulfoxonium iodideRelated Search:

Propidium iodide Dimethyl sulfoxide TRIMETHYLSULFOXONIUM BROMIDE Trimethylsulfonium iodide TRIMETHYLSULFOXONIUM CHLORIDE Potassium iodide 1-METHYL-1,2,4-TRIAZOLE Triphenylphosphine Hexadecyl trimethyl ammonium bromide TRI-N-BUTYLPHOSPHINE OXIDE Tri(o-tolyl)phosphine tert-Butyl(triphenylphosphoranylidene)acetate Trityl losartan TRIETHYLSILANOL Origanum oil BETA-GLUCAN Fluconazole 2-(2-fluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol

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