54828-68-1

Basic information

• Product Name: Benzene, 1-[(R)-ethenylsulfinyl]-4-methyl-
• CAS NO: 54828-68-1
• Molecular Formula: C9H10OS
• Molecular Weight: 166.244
• Mol File: 54828-68-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(R)-ethenylsulfinyl]-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(R)-ethenylsulfinyl]-4-methyl-(54828-68-1)
• EPA Substance Registry System: Benzene, 1-[(R)-ethenylsulfinyl]-4-methyl-(54828-68-1)

Safety Data

• Hazardous Substances Data: 54828-68-1(Hazardous Substances Data)

Upstream product

• 79-24-3 Nitroethane 
• 36832-47-0 vinyl-4-tolylsulfoxide 
• 16336-54-2 p-tolyl vinyl sulfide 
• 106-45-6 para-thiocresol 
• 98147-48-9 2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 1826-67-1 vinyl magnesium bromide 
• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 3536-96-7 vinylmagnesium chloride 
• 190448-84-1 (1S,5R,7R)-10,10-Dimethyl-4-((R)-toluene-4-sulfinyl)-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 50-00-0 formaldehyd 
• 61187-71-1 (+)-(R)-(dimethoxyphosphoryl)methyl p-tolyl sulfoxide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 59336-80-0 1,2-Dibrom-1-p-tolylsulfinylethan 
• 128176-13-6 (S)_S-4-methyl-2-p-tolylsulfinyl-1-penten-3-ol 
• 107647-71-2 (R)_S-dimethylamino-2 p-tolylsulfinyl-1 ethane 
• 107647-76-7 1-Phenyl-2-((S)-toluene-4-sulfinyl)-prop-2-en-1-ol 
• 89279-83-4 (1S,4S,5R)-5-((R)-Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-2-ene 
• 89279-83-4 (1R,4R,5R)-5-((R)-Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-2-ene 
• 142048-22-4 2-ethoxyethyl p-tolyl (R_S)-sulfoxide 
• 52266-42-9 2-methyl-3-phenyl-4-isoxazoline 
• 82769-70-8 (3S,4S)-2-Methyl-3-phenyl-4-((R)-toluene-4-sulfinyl)-isoxazolidine 
• 139730-35-1 (1S,5S,6S)-8-Methyl-6-(toluene-4-sulfinyl)-8-aza-bicyclo[3.2.1]oct-3-en-2-one 
• 139730-35-1 (1R,5R,6S)-8-Methyl-6-(toluene-4-sulfinyl)-8-aza-bicyclo[3.2.1]oct-3-en-2-one 
• 139730-35-1 (1S,5S,6R)-8-Methyl-6-(toluene-4-sulfinyl)-8-aza-bicyclo[3.2.1]oct-3-en-2-one 
• 139730-35-1 N-methyl-(1R,5R,6S,R_S)-6-(p-tolylsulphinyl)-8-azabicyclo<3.2.1>oct-3-en-2-one 
• 139730-37-3 N-methyl-(1S,5S,6R,R_S)-6-(p-tolylsulphinyl)-8-azabicyclo<3.2.1>oct-3-en-2-one 

Relevant articles and documents

Synthesis of N-tetrasubstituted cyclam derivatives appended with sulfonyl or sulfinyl groups via aza-Michael addition

Azamacrocycles bearing four arylsulfonyl or arylsulfinyl pendant arms have been synthesised with good yields through nucleophilic addition of 1,4,8,11-tetraazacyclotetradecane (cyclam) to phenylvinylsulfone, phenylvinylsulfoxide or (R)-tolylvinylsulfoxide

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.

Stereoselective synthesis of racemic and optically active E-vinyl and E- dienyl sulfoxides via Wittig reaction of α-sulfinyl phosphonium ylides

A series of α-sulfinyl phosphonium ylides have been obtained in the reaction of phosphonium mono- and diylides with sulfinic acid esters. The use of (-)-(S)-menthyl p-toluenesulfinate in this reaction afforded the corresponding (S)-((p-tolylsulfinyl)methyl)triphenylphosphonium ylide. The Wittig reaction of these ylides with saturated and unsaturated aldehydes resulted in the formation of racemic and optically active (+)-(R)-vinyl and dienyl sulfoxides with the E-geometry. The synthesis of (+)-(R)-((p- tolylsulfinyl)methyl)triphenylphosphonium iodide as a precursor of the optically active ylide has also been described.