188447-75-8

Basic information

• Product Name: 4-Methyl-benzenesulfinic acid [1-phenyl-eth-(E)-ylidene]-amide
• Synonyms: 4-Methyl-benzenesulfinic acid [1-phenyl-eth-(E)-ylidene]-amide
• CAS NO: 188447-75-8
• Molecular Weight: 257.356
• Mol File: 188447-75-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Methyl-benzenesulfinic acid [1-phenyl-eth-(E)-ylidene]-amide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-benzenesulfinic acid [1-phenyl-eth-(E)-ylidene]-amide(188447-75-8)
• EPA Substance Registry System: 4-Methyl-benzenesulfinic acid [1-phenyl-eth-(E)-ylidene]-amide(188447-75-8)

Safety Data

• Hazardous Substances Data: 188447-75-8(Hazardous Substances Data)

Upstream product

• 177265-17-7 C₁₅H₁₅NS 
• 917-54-4 methyllithium 
• 1517-82-4 (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate 
• 100-47-0 benzonitrile 

Downstream Products

• 131154-18-2 (-)-(S)-1-methyl-1-phenyl-3-butenamine 
• 131154-31-9 (R)-4-Acetylamino-4-phenyl-pentanoic acid 
• 131154-29-5 N-((R)-4-Hydroxy-1-methyl-1-phenyl-butyl)-acetamide 
• 131154-33-1 (R)-4-Amino-4-phenyl-pentanoic acid 
• 131154-23-9 N-((R)-1-Methyl-1-phenyl-but-3-enyl)-acetamide 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 131154-15-9 4-Methyl-benzenesulfinic acid ((S)-1-methyl-1-phenyl-but-3-enyl)-amide 
• 866993-59-1 (2R,3S)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]butyl-2-amine 
• 177468-98-3 (-)-(S)(C)-(R)(S)-N-(1-Phenylethyl)-p-toluolsulfinamid 
• 866993-66-0 [2S,3S,(S)R]-N-{2-pheny-3-triisopropylsilyloxy-3-[(S)-2-(p-toluenesulfinyl)phenyl]propyl}-p-toluenesulfinamide 

Relevant articles and documents

Asymmetric Synthesis Properties of Sulfinimines (Thiooxime S-Oxides)

Enantiomerically pure sulfinimines (thiooxime S-oxides 10), important building blocks in the asymmetric synthesis of amine derivatives, are prepared in good to excellent yields in one step from aromatic, heteroaromatic, and aliphatic aldehydes. This protocol involves treating commercially available (R)- or (S)-menthyl p-toluenesufinate (Andersen reagent 4) with LiHMDS, followed by the aldehyde, affording (E)-10 exclusively. The sulfinimines 10 are formed via a Peterson-type olefination reaction of silylsulfinamide anion 13 with the aldehyde. Anion 13 is generated by reaction of lithium menthoxide (12a) with bis(trimethylsilyl)sulfinamide 11, which is formed in the reaction of 4 with LiHMDS. The other product formed is O-(trimethylsilyl)menthol (12c), which is isolated in >80% yield for recycling. Two other less efficient methods for the asymmetric synthesis of 10 are discussed: (i) the asymmetric oxidation of sulfenimines 6 with chiral nonracemic oxaziridines and (ii) the reaction of metal aldimines, prepared from nitriles, with 4. All of these protocols fail with ketones.

Stereoselective Addition Reactions of Chiral N-Benzylidene-p-toluenesulfinamides. Asymmetric Syntheses of β- and γ-Amino Acids

Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitril with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate.Treatment of 2 with allylmagnesium bromide in ether at 0 deg C gave the adducts (R)-7 with excellent stereoselectivity.Pure chiral sulfinamides 7 were converted into β- and γ-amino acids in four and five steps, respectively.