142048-22-4

Basic information

• Product Name: Benzene, 1-[(2-ethoxyethyl)sulfinyl]-4-methyl-, (R)-
• CAS NO: 142048-22-4
• Molecular Formula: C11H16O2S
• Molecular Weight: 212.313
• Mol File: 142048-22-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(2-ethoxyethyl)sulfinyl]-4-methyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(2-ethoxyethyl)sulfinyl]-4-methyl-, (R)-(142048-22-4)
• EPA Substance Registry System: Benzene, 1-[(2-ethoxyethyl)sulfinyl]-4-methyl-, (R)-(142048-22-4)

Safety Data

• Hazardous Substances Data: 142048-22-4(Hazardous Substances Data)

Upstream product

• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 64-17-5 ethanol 
• 54828-68-1 (R)-p-tolyl vinyl sulfoxide 
• 141-52-6 sodium ethanolate 

Downstream Products

• 143031-92-9 (S)_S-2-methyl-3-p-tolylsulfinyl-3-buten-2-ol 
• 142079-86-5 Methanesulfonic acid 1-methyl-2-((S)-toluene-4-sulfinyl)-allyl ester 
• 142048-19-9 (+)-(R)-2-p-toluenesulfinyl-1,3-butadiene 
• 107647-81-4 (S_S)-3-(p-tolylsulfinyl)-3-buten-2-one 
• 107647-75-6 (+)-(S)-3-(p-tolylsulfinyl)-3-buten-2-ol 
• 235100-20-6 (S)_S-3-p-tolylsulfinyl-3-buten-2-ol 
• 143031-91-8 (+)-(S)-1-(3',4'-dimethoxyphenyl)-2-(p-tolylsulfinyl)-2-propen-1-ol 
• 107647-85-8 (+)-(S)-1-<1-(p-tolylsulfinyl)ethenyl>cyclohexan-1-ol 
• 107647-82-5 (+)-(S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-one 
• 152836-27-6 2-(p-tolylsulfinyl)pent-1-en-3-ol 

Relevant articles and documents

Highly stereoselective asymmetric pummerer reactions that incorporate intermolecular and intramolecular nonbonded S...O interactions

New chiral sulfoxides (RS,S)-3, (SS,S)-3, (R S,S)-4, and (SS,S)-4 and known chiral sulfoxides (R S)-5, (RS)-6, and (RS)-7 were synthesized, and the stereochemistry of the new sulfoxides (RS,S)-3 and (R S,S)-4 was determined by X-ray crystallographic analysis. In their crystallographic structures, the intramolecular nonbonded S...O close contacts were recognized. Analyses of several sulfoxide complexes including rac-11 with N,N-dimethylacetamide (DMAC) or N-methyl-2-pyrrolidone (NMP) in a MeOH solution utilizing cold-spray ionization mass spectrometry provided, for the first time, direct information for intermolecular nonbonded S...O interactions between sulfoxides and amide (or lactam) in a solution. Highly diastereoselective and enantioselective Pummerer reactions based on the concept of intermolecular and intramolecular nonbonded S...O interactions were performed by treatment of several chiral sulfoxides (RS, S)-3, (SS, S)-3, (RS, S)-4, (SS, S)-4, (R S)-5, (RS)-6, and (RS)-7 with acetic anhydride and trimethylsilyl triflate (TMSOTf) in DMAC, NMP, N,N-dimethylformamide, and N-formylpiperidine. Mechanistic studies on these facile stereoselective Pummerer reactions revealed the necessity for the amide/TMSOTf complex, such as 26 or 27, to be an efficient activation reagent for Ac2O and a trapping reagent for the released acetate ion, and that DMAC and NMP had a positive effect on this highly stereoselective chiral transfer reaction.