CAS RN: 1352947-66-0 | Product Number: M2274
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|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|
|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 %|
|Solubility (slightly sol. in)||Methanol|
|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.
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)
- 1)D. Tsuchiya, M. Tabata, K. Moriyama, H. Togo, Tetrahedron 2012, 68, 6849.
- 2)D. Tsuchiya, K. Moriyama, H. Togo, Synlett 2011, 2701.
- 3)H. Togo, TCIMAIL 2013, number 157, 2. [PDF : 2.2MB]
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