93222-06-1

Basic information

• Product Name: Benzene, 1-(methylsulfinyl)-4-nitro-, (R)-
• CAS NO: 93222-06-1
• Molecular Formula: C7H7NO3S
• Molecular Weight: 185.203
• Mol File: 93222-06-1.mol
• Article Data: 72

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(methylsulfinyl)-4-nitro-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(methylsulfinyl)-4-nitro-, (R)-(93222-06-1)
• EPA Substance Registry System: Benzene, 1-(methylsulfinyl)-4-nitro-, (R)-(93222-06-1)

Safety Data

• Hazardous Substances Data: 93222-06-1(Hazardous Substances Data)

Upstream product

• 701-57-5 1-methylthio-4-nitro-benzene 
• 75-16-1 methylmagnesium bromide 
• 940-12-5 p-nitrophenyl methyl sulfoxide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 164021-74-3 (1S,2R)-(-)-2-[N-(3’,5’-di-tert-butylsalicylidene)amino]-1,2-diphenylethanol 

Downstream Products

• 125761-96-8 (R)-(+)-Methyl <(4-nitrophenyl)sulfinyl>acetate 

Relevant articles and documents

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Chiral: N, N ′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide

A highly enantioselective sulfoxidation of various sulfides has been achieved by a N,N′-dioxide-iron(iii) complex with 35% aq. H2O2 as the oxidant. The utility of the current method was demonstrated by asymmetric gram-scale synthesis of drug molecule (R)-modafinil. Moreover, a possible working mode was provided to elucidate the chiral induction.

Bio-inspired single-chain polymeric nanoparticles containing a chiral salen TiIV complex for highly enantioselective sulfoxidation in water

A series of bio-inspired single-chain polymeric nanoparticles (SCPNs) containing a chiral salen TiIV complex in their hydrophobic cavity were constructed from the synthesized amphiphilic copolymers of poly(NIPAAm-co-IL/Ti(salen)) (NIPAAm, N-isopropylacrylamide; IL/Ti(salen), vinylimidazolium ionic liquid-modified chiral salen TiIV complex). These SCPNs behaved as enzyme-mimetic catalysts due to compartmentalization and site isolation, mediating enantioselective oxidation of various sulfides in water with excellent yields (90-99%) and enantioselectivities (ee, 88-99%). In particular, the ee values observed for electron-rich substrates (>95% ee) represented the best results so far in titanium-salen systems. Moreover, the catalysts could be easily recovered for steady reuse by thermo-controlled separation due to thermo-responsive properties. This work first constructed titanium-containing biomimetic SCNPs for biocatalysis of enantioselective sulfoxidation in water.