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1-Methyl-3-[6-(methylthio)hexyl]imidazolium p-Toluenesulfonate
(CAS RN:1352947-63-7 Product Number:M2321)

Structure

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

General Information

Product Number M2321

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Purity/Analysis Method >95.0%(HPLC)(N)
Storage Temperature
M.F. / M.W. C18H28N2O3S2=384.55
CAS RN 1352947-63-7
Related CAS RN
MDL Number
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Purity(HPLC) min. 95.0 area%
Purity(with Total Nitrogen) min. 95.0 %

References

Reaxys-RN 22038359
PubChem SID 160871261

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

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 ºC, 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 ºC. The mixture is stirred at-20 or -40 ºC 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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