TRIMETHYLSULFOXONIUM CHLORIDE

Base Information

• Chemical Name: TRIMETHYLSULFOXONIUM CHLORIDE
• CAS No.: 5034-06-0
• Molecular Formula: C3H9ClOS
• Molecular Weight: 128.623
• Hs Code.: 29309099
• European Community (EC) Number: 225-724-6
• NSC Number: 221182
• UNII: KV8UUA9PBU
• Mol file: 5034-06-0.mol

Synonyms:Trimethylsulfoniumchloride, oxide (6CI,7CI);NSC 221182;Trimethyloxosulfonium chloride;Trimethylsulfoxonium chloride;

Chemical Property of TRIMETHYLSULFOXONIUM CHLORIDE

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 226-229 °C(lit.)
• PSA: 36.28000
• LogP: -2.62070
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Sonicated), Water (Sparingly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.0062638
• Heavy Atom Count: 6
• Complexity: 53

Purity/Quality:

99% ^*data from raw suppliers

Trimethylsulfoxonium chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[S+](=O)(C)C.[Cl-]
• Uses: Reactant involved in:Polymerization of ylidesX-H insertionOne-pot sequential additionCyclopropanation of enones

Technology Process of TRIMETHYLSULFOXONIUM CHLORIDE

There total 3 articles about TRIMETHYLSULFOXONIUM CHLORIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

trimethylsulfoxonium iodide (1774-47-6) → trimethyl sulfoxonium chloride (5034-06-0)

Guidance literature:

With benzyltri(n-butyl)ammonium chloride; In dichloromethane; water; for 17h;

DOI:10.1021/ja017376c

Reference yield: 61.0%

3-chloro-2-methoxycyclohex-2-en-1-one (35155-66-9) + dimethylsulfoxonium methylide (70775-39-2,5367-24-8) → trimethyl sulfoxonium chloride (5034-06-0) + dimethyloxosulphonium (2-methyl-3-oxocyclohex-1-en-1-yl)methylide (73801-71-5)

Guidance literature:

In tetrahydrofuran; for 18h; Heating;

DOI:10.1039/P19810003225

Reference yield:

ruthenium(IV) oxide hydrate + trimethylsulfonium chloride (3086-29-1) → trimethyl sulfoxonium chloride (5034-06-0)

Guidance literature:

In water;

upstream raw materials:

3-chloro-2-methoxycyclohex-2-en-1-one

dimethylsulfoxonium methylide

trimethylsulfoxonium iodide

trimethylsulfonium chloride

Downstream raw materials:

(3aΞ,5aR)-4c-methoxy-2-(4-nitro-phenyl)-8c-phenyl-(5ar,9at)-2,3a,4,5a,6,9a-hexahydro-3H-[1,3]dioxino[4',5':5,6]pyrano[4,3-c]pyrazole

1,6-dioxa-spiro[2.5]octane

2-Butyl-2-((Z)-1-fluoro-2-phenyl-vinyl)-oxirane

1-(4-chlorophenyl)-2-(dimethyl(oxo)-λ⁶-sulfanylidene)ethan-1-one

Refernces

Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide promoted by a La-Li₃-(Biphenyldiolate)₃ + NaI complex

10.1021/ja076797c

The study presents a novel catalytic asymmetric cyclopropanation reaction of enones using dimethyloxosulfonium methylide, promoted by a La-Li3-(biphenyldiolate)3 + NaI complex. The reaction showcases high enantioselectivity, with up to 99% ee, and is applicable to a variety of enones, including those with electron-withdrawing or electron-donating substituents and heteroaryl-substituted enones. The use of NaI as an additive, along with biphenyldiol as a ligand, is crucial for achieving this level of selectivity. The reaction conditions were optimized to allow for slow addition of enones, which further improved the enantioselectivity. The study also explores the potential of the catalyst system with other substrates, such as an N-acylpyrrole, and discusses the role of NaI in the reaction mechanism, suggesting a partial alkali metal exchange occurs in situ to form a La-Li2-Na-(biphenyldiolate)3 complex. The findings provide a complementary approach to existing methods for catalytic asymmetric cyclopropanation and highlight the importance of the mixed-alkali metal system in achieving high yields and enantioselectivity.

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