22236-45-9

Basic information

• Product Name: S,S-DIMETHYL-N-(P-TOLUENESULFONYL)SULFOXIMINE
• Synonyms: S,S-DIMETHYL-N-(P-TOLUENESULPHONYL)SULPHOXIMINE;RARECHEM AQ A1 0067;N-(p-Toluenesulphonyl)dimethylsulphoximine;S,S-dimethyl-N-(p-tolylsulphonyl)sulphoximide;n-(p-toluenesulfonyl)dimethylsulfoximine;S,S-Dimethyl-N-(4-methylphenylsulfonyl)sulfoximide;S,S-Dimethyl-N-[(4-methylphenyl)sulfonyl]sulfoximide;Nsc202395
• CAS NO: 22236-45-9
• Molecular Formula: C₉H₁₃NO₃S₂
• Molecular Weight: 247.33
• EINECS: 244-861-2
• Mol File: 22236-45-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 167-169 °C(lit.)
• Boiling Point: 390.8°Cat760mmHg
• Flash Point: 190.1°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 5.83E-06mmHg at 25°C
• Refractive Index: 1.557
• Solubility: Soluble in EtOH, THF, DMSO.
• BRN: 2119329
• CAS DataBase Reference: S,S-DIMETHYL-N-(P-TOLUENESULFONYL)SULFOXIMINE(CAS DataBase Reference)
• NIST Chemistry Reference: S,S-DIMETHYL-N-(P-TOLUENESULFONYL)SULFOXIMINE(22236-45-9)
• EPA Substance Registry System: S,S-DIMETHYL-N-(P-TOLUENESULFONYL)SULFOXIMINE(22236-45-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 22236-45-9(Hazardous Substances Data)

Usage

Uses

S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, is used as methylene-transfer agent. The anion adds to carbonyl compounds to give epoxides which can react with a further mole of reagent with ring expansion to give 2,2-disubstituted oxetanes. It is also used as a pharmaceutical intermediate.

InChI:InChI=1/C9H13NO3S2/c1-8-4-6-9(7-5-8)15(12,13)10-14(2,3)11/h4-7H,1-3H3

Upstream product

• 1520-31-6 dimethylsulfoximine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1593-60-8 p-toluenesulfonylhydroxylamine 
• 127-65-1 chloroamine-T 
• 67-68-5 dimethyl sulfoxide 
• 24698-06-4 S-p-nitrophenyl-S-phenyl-N-tosylsulfilimine 
• 24230-23-7 N-(4-Nitro-benzolsulfonyloxy)-toluol-4-sulfonamid 
• 941-55-9 4-toluenesulfonyl azide 
• 13150-75-9 S,S-dimethyl-N-p-tolylsulfonylsulfimine 

Downstream Products

• 42153-88-8 S-Methyl-S-(2-amino-2-phenylvinyl)-N-(p-tolylsulfonyl)sulfoximin 
• 42153-89-9 1-phenyl-2--1-ethanone 
• 72174-74-4 1-phenyl-2-ethanol 
• 72174-68-6 S-methyl-S-(trans-2-phenylethenyl)-N-(p-tolylsulfonyl)sulfoximine 
• 42153-90-2 N,N'-Di-p-tolyl-N-(p-tolylsulfonylmethylsulfonimidoyl)acetamidin 
• 1520-31-6 dimethylsulfoximine 

Relevant articles and documents

Copper-catalyzed imination of sulfoxides and sulfides

Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.

General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor

The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clinical candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesising a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, commercially available precursor is discussed.

Preparation of N-(Arylsulfonyl)sulfoximines by Oxidation of N-(Arylsulfonyl)sulfilimines with Sodium Hypochlorite in a Two-Phase System

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