60933-65-5

Basic information

• Product Name: (R)-(-)-S-METHYL-S-PHENYLSULFOXIMINE
• Synonyms: (R)-(-)-S-Methyl-S-phenylsulfoximine99%ee;(R)-(-)-S-METHYL-S-PHENYLSULFOXIMINE;(R)-(-)-S-METHYL-S-PHENYLSULPHOXIMINE
• CAS NO: 60933-65-5
• Molecular Formula: C₇H₉NOS
• Molecular Weight: 155.22
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Sulfur-Based
• Mol File: 60933-65-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 29-31°C
• Boiling Point: 237.8 °C at 760 mmHg
• Flash Point: 97.6 °C
• Appearance: /
• Density: 1.14 g/cm³
• Sensitive: Hygroscopic
• BRN: 5245635
• CAS DataBase Reference: (R)-(-)-S-METHYL-S-PHENYLSULFOXIMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-S-METHYL-S-PHENYLSULFOXIMINE(60933-65-5)
• EPA Substance Registry System: (R)-(-)-S-METHYL-S-PHENYLSULFOXIMINE(60933-65-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 60933-65-5(Hazardous Substances Data)

Usage

Uses

(R)-(-)-S-Methyl-S-phenylsulfoximine is used as chiral ligands.

Upstream product

• 4381-25-3 S-methyl-S-phenylsulfoximine 
• 36789-47-6 S-Methyl-S-phenyl-N-carboethoxysulfoximid 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 1039027-81-0 (S)-N-cyclohex-1-enyl-S-methyl-S-phenylsulfoximine 
• 7044-59-9 C₁₀H₁₆O₄S*C₇H₉NOS 
• 882-33-7 diphenyldisulfane 
• 4972-29-6 benzenesulphinyl chloride 
• 100-68-5 methyl-phenyl-thioether 
• 2725-60-2 1-(p-methylphenylsulfonyl)-1-diazopropan-2-one 
• 131505-03-8 ethyl 3-cyclopropyl-2-diazo-3-oxopropanoate 
• 823182-69-0 ethyl 2-diazo-3-(furan-2-yl)-3-oxopropanoate 
• 89861-36-9 ethyl (4E)-2-diazo-3-oxo-5-phenylpent-4-enoate 
• 28383-65-5 ethyl 2-diazo-3-oxo-3-phenylpropanoate 
• 13298-76-5 tert-butyl 2-diazo-3-oxobutanoate 

Downstream Products

• 65975-55-5 (-)-(R)-Methylphenyloxosulfonium-bis-(methoxycarbonyl)-methylid 
• 100326-79-2 (-)-(R)-1,5-diphenyl-1H-1λ⁴,2,4-thiadiazine 1-oxide 
• 100326-78-1 (+)-(S)-1,5-diphenyl-1H-1λ⁴,2,4-thiadiazine 1-oxide 
• 42153-74-2 S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfoximide 
• 42153-74-2 (+)-(S_S)-S-methyl-S-phenyl-N-(p-tolylsulphonyl)sulphoximine 
• 152983-29-4 (+)-(S_S)-S-methyl-S-phenyl-N-(trimethylsilyl)sulfoximine 
• 33993-53-2 N,S-dimethyl-S-phenylsulfoximine 
• 188633-73-0 (S_S)-N-(N-tert-Butyloxycarbonyl-L-prolinyl)-S-methyl S-phenyl sulfoximine 
• 188633-70-7 (S_S)-N-(N-tert-Butyloxycarbonyl-L-valinyl)-S-methyl S-phenyl sulfoximine 
• 188633-72-9 (S_S)-N-(N-tert-Butyloxycarbonyl-L-isoleucinyl)-S-methyl S-phenyl sulfoximine 
• 188633-71-8 (S_S)-N-(N-tert-Butyloxycarbonyl-L-leucinyl)-S-methyl S-phenyl sulfoximine 
• 654084-10-3 C₁₃H₁₁BrN₂O₂S 

Relevant articles and documents

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid

Ru(II)-catalyzed enantioselective C-H functionalization involving an enantiodetermining C-H cleavage step remains undeveloped. Here we describe a Ru(II)-catalyzed enantioselective C-H activation/annulation of sulfoximines with α-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, which can be easily and modularly prepared from 1,1′-binaphthyl-2,2′-dicarboxylic acid. A broad range of sulfur-stereogenic sulfoximines were prepared in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution. Furthermore, the resolution products can be easily transformed to chiral sulfoxides and key intermediates for kinase inhibitors.

Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents

Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sul

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.