22132-99-6

Basic information

• Product Name: S-METHYL-S-(4-CHLOROPHENYL) SULFOXIMINE
• Synonyms: S-METHYL-S-(4-CHLOROPHENYL) SULFOXIMINE;1-Chloro-4-(S-methylsulfonimidoyl)benzene;(4-Chlorophenyl)(imino)(methyl)-l6-sulfanone
• CAS NO: 22132-99-6
• Molecular Formula: C₇H₈ClNOS
• Molecular Weight: 189.66252
• Mol File: 22132-99-6.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: S-METHYL-S-(4-CHLOROPHENYL) SULFOXIMINE(CAS DataBase Reference)
• NIST Chemistry Reference: S-METHYL-S-(4-CHLOROPHENYL) SULFOXIMINE(22132-99-6)
• EPA Substance Registry System: S-METHYL-S-(4-CHLOROPHENYL) SULFOXIMINE(22132-99-6)

Safety Data

• Statements: 22
• Safety Statements: 24/25
• Hazardous Substances Data: 22132-99-6(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Upstream product

• 655-20-9 2-fluorothioanisole 
• 1111-78-0 ammonium carbamate 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 934-73-6 methyl 4-chlorophenyl sulfoxide 
• 106-54-7 p-Chlorothiophenol 

Downstream Products

• 35539-98-1 C₉H₁₀ClNO₂S 
• 35539-67-4 C₁₄H₁₃ClN₂O₂S 
• 35539-69-6 C₉H₁₀ClN₃O₄S 
• 1584154-59-5 (benzhydrylimino)(4-chlorophenyl)(methyl)-λ⁶-sulfanone 
• 67087-50-7 N-methyl-S-(4-chlorophenyl)-S-methylsulfoximine 

Relevant articles and documents

Electrochemical Oxidative Syntheses of NH-Sulfoximines, NH-Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates

Herein, we report a general method for the synthesis of NH-sulfoximines and NH-sulfonimidamides through direct electrochemical oxidative catalysis involving an iodoarene(I)/iodoarene(III) redox couple. In addition, dibenzothiazines can be synthesized from [1,1′-biaryl]-2-sulfides under standard conditions. Notably, only a catalytic amount of iodoarene is required for the generation in situ of an active hypervalent iodine catalyst, which avoids the need for an excess of a hypervalent iodine reagent relative to conventional approaches. Moreover, this protocol features broad substrate scope and wide functional group tolerance, delivering the target compounds with good-to-excellent yields even for a scale of more than 10 g.

Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions

The synthesis of NH-sulfoximines from sulfides has been first developed under mild conditions in an aqueous solution with surfactant TPGS-750-M as the catalyst at room temperature. In this newly developed process, a simple and convenient recycling strategy to regenerate the indispensable hypervalent iodine(III) is used. The resulting 1,2,3-trifluoro-5-iodobezene can be recovered almost quantitively from the mixture by liquid–liquid extraction and then oxidized to give the corresponding iodine(III) species. This optimized procedure is compatible with a broad range of functional groups and can be easily performed on a gram scale, providing a green protocol for the synthesis of sulfoximines.

Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting CpXRhIII-Catalyzed C?H Functionalization

Chiral sulfoximines with stereogenic sulfur atoms are promising motifs in drug discovery. We report an efficient method to access chiral sulfoximines through a C?H functionalization based kinetic resolution. A rhodium(III) complex equipped with a chiral Cpx ligand selectively participates in conjunction with phthaloyl phenylalanine in the C?H activation of just one of the two sulfoximine enantiomers. The intermediate reacts with various diazo compounds, providing access to chiral 1,2-benzothiazines with synthetically valuable substitution patterns. Both sulfoximines and 1,2-benzothiazines were obtained in high yields and excellent enantioselectivity, with s-values of up to 200. The utility of the method is illustrated by the synthesis of the key intermediates of two pharmacologically relevant kinase inhibitors.