Trimethylsulfoxonium iodide #CAS1774-47-6

Trimethylsulfoxonium iodide #CAS1774-47-6

Trimethylsulfoximine is a white to pale yellow crystalline substance. It is soluble in water and dimethyl sulfoxide, and slightly soluble in methanol.

It is a typical sulfide salt organic metal precursor and a sulfoxonium ylide precursor. In terms of properties, it exhibits a high melting point, relative stability to water and air, and is a white crystalline solid. Due to the positively charged central sulfur atom, it shows strong electrophilicity and can slightly dissolve in water and easily dissolve in strong polar non-aqueous solvents such as dimethyl sulfoxide (DMSO). The most crucial chemical activity of this compound lies in the significant weak acidity of the methyl hydrogen in its structure. Under the action of strong bases such as sodium hydride and tert-butyl alcohol potassium, it can instantly undergo deprotonation and in situ generate a strong nucleophilic dimethyl sulfoxide methylene sulfoxonium ylide (Corey-Chaykovsky reagent). This active sulfoxonium ylide can efficiently undergo nucleophilic addition to the electrophilic carbon atoms of aldehydes, ketones, and imines, and then undergo stepwise elimination through dimethyl sulfoxide (DMSO) as an excellent leaving group, selectively constructing a tricyclic skeleton (such as epoxides, cyclopropane derivatives, and nitrogen-containing cyclopropanes). Moreover, it is prone to decomposition under high temperature or strong light and releases corrosive and toxic hydrogen iodide (HBr/HI) and toxic sulfur oxides gases. Therefore, it needs to be sealed and stored under normal temperature, dry conditions, and avoiding contact with strong bases and strong oxidants in a sealed environment.

Application Of Trimethylsulfoxonium iodide

Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5

Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides.

Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

It is mainly used as a key core reagent and special functional additive for synthesizing fine chemicals, pharmaceutical intermediates, and agricultural chemicals. In the pharmaceutical industry and the fine synthesis of pesticides, it serves as the core raw material for the renowned "Corey-Chaykovsky reaction", and is widely used for in-situ production of thiophenyl active intermediates, thereby enabling high selectivity and high yield to industrially construct cycloalkenes and cyclopropene drug frameworks (such as the core structures of certain antiviral drugs, cardiovascular drugs, and pyrethroid insecticides); moreover, due to its molecules containing specific quaternary锍 cation ions and iodide anions， it is also commonly used in the organic polymer and petrochemical fields as a hardening accelerator for special plastics and resins， a photopolymerization initiator， an organic electrolyte additive， and an efficient homogeneous catalyst or a precursor for phase transfer catalysis， which can significantly optimize the rate of specific industrial polymerization reactions and the microscopic physical properties of the products.

Fact Factory and Equipment Show