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CAS RN: 1352947-66-0 | Product Number: M2274

1-Methyl-3-[6-(methylsulfinyl)hexyl]imidazolium p-Toluenesulfonate

Purity: >97.0%(HPLC)(N)
  • 1-Methyl-3-[6-(methylsulfinyl)hexyl]imidazolium Tosylate
2   6  
1   13  

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Product Number M2274
Purity / Analysis Method >97.0%(HPLC)(N)
Molecular Formula / Molecular Weight C__1__8H__2__8N__2O__4S__2 = 400.55  
Physical State (20 deg.C) Liquid
Store Under Inert Gas Store under inert gas
Condition to Avoid Hygroscopic
CAS RN 1352947-66-0
PubChem Substance ID 172088958
Appearance Colorless to Light orange to Yellow clear liquid
Purity(HPLC) min. 97.0 area%
Purity(with Total Nitrogen) min. 97.0 %
Properties (reference)
Solubility (slightly sol. in) Methanol
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws:
Transport Information:
HS Number 2933299090
Efficient and Odorless Swern Oxidation with Recoverable Ion-Supported Methyl Sulfoxide

Typical procedure:
Oxalyl chloride (0.34 mL, 4.0 mmol) is added dropwise to a solution of 1-methyl-3-[6-(methylsulfinyl)hexyl]imidazolium p-toluenesulfonate (1.60 g, 4.0 mmol) in CH2Cl2 (6 ml) at -70 °C and the mixture is stirred for 30 min. Then, a solution of alcohol (2.0 mmol) in CH2Cl2 (3 mL) is added dropwise at -70 °C and stirred for 30 min. Triethylamine (1.66 mL, 12 mmol) is added dropwise at -70 °C and the mixture is stirred for 1 h at -70 °, 1.5 h at -60 °C, and then -50 °C for 1 h. Finally, the mixture is warmed to room temperature and stirred for 2 h. The reaction mixture is quenched with H2O (10 mL), neutralized (pH = 6 to 7) with 1 M HCl aqueous solution, and extracted with diethyl ether (40 mL × 2). The organic layer is washed with water (10 mL), dried over Na2SO4, and filtered. After removal of the solvent, the desired aldehyde or ketone is obtained.

Recovery and recycling of ion-supported methyl sulfoxide: After the above extraction, the aqueous layer is concentrated in vacuo. After the addition of aqueous saturated NaHCO3 solution, the ion-supported methyl sulfide is extracted with CHCl3 (40 mL × 3). The organic layer is dried over Na2SO4 and filtered. After removal of the solvent, the residue is washed with diethyl ether (10 mL × 3), and concentrated in vacuo to give the ion-supported methyl sulfide in 73% yield. The methyl sulfide is quantitatively oxidized to 1-methyl-3-[6-(methylsulfinyl)hexyl]imidazolium p-toluenesulfonate according to the literature.1)


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