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CAS RN: 1352947-63-7 | Product Number: M2321

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


Purity: >95.0%(HPLC)(N)
Synonyms:
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Product Number M2321
Purity / Analysis Method >95.0%(HPLC)(N)
Molecular Formula / Molecular Weight C__1__8H__2__8N__2O__3S__2 = 384.55  
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Hygroscopic
CAS RN 1352947-63-7
Reaxys Registry Number 22038359
PubChem Substance ID 160871261
Specifications
Appearance White to Almost white powder to crystal
Purity(HPLC) min. 95.0 area%
Purity(with Total Nitrogen) min. 95.0 %
Properties (reference)
Solubility in water Slightly soluble
GHS
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
Application
Efficient and Odorless Corey–Kim Oxidation with Recoverable Ion-Supported Methyl Sulfide

Typical procedure: A solution of 1-methyl-3-[6-(methylthio)hexyl]imidazolium p-toluenesulfonate (0.769 g, 2.0 mmol) and the starting alcohol (1.0 mmol) in CH2Cl2 (6 mL) is added to a CH2Cl2 (5 mL) solution of N-chlorosuccinimide (0.267 g, 2.0 mmol) at -20 or -40 °C, and the mixture is stirred for 0.5 h. Triethylamine (0.506 g, 5.0 mmol) is added to the mixture at -20 or -40 °C. The mixture is stirred at-20 or -40 °C for 14 h, quenched with H2O (20 mL), and extracted with diethyl ether (60 mL). The organic layer is washed with H2O (20 mL) and a saturated aqueous NaHCO3 (30 mL×2). The organic layer is dried over Na2SO4 and concentrated in vacuo to give the desired aldehyde or ketone.

Recovery of 1-methyl-3-[6-(methylthio)hexyl]imidazolium p-toluenesulfonate: After the above extraction, the aqueous layer is concentrated in vacuo. Then, KI (0.332 g, 2.0 mmol), AcOH (2 mL) and TsOH· H2O (0.379 g, 2.2 mmol) are added to the residue at room temperature. The mixture is stirred for 1 h, quenched with a saturated aqueous Na2SO3 (5 mL) and a saturated aqueous NaHCO3 (5 mL), and extracted with CHCl3 (40 mL×3). The organic layer is dried over Na2SO4 and concentrated in vacuo to give 1-methyl-3-[6-(methylthio)hexyl]imidazolium p-toluenesulfonate (0.646 g, 84%).

References


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