123299-91-2

Basic information

• Product Name: (R)-2-(phenylsulfinyl)ethanol
• Synonyms: (R)-2-(phenylsulfinyl)ethanol
• CAS NO: 123299-91-2
• Molecular Weight: 170.232
• Mol File: 123299-91-2.mol
• Article Data: 124

Chemical Properties

• CAS DataBase Reference: (R)-2-(phenylsulfinyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(phenylsulfinyl)ethanol(123299-91-2)
• EPA Substance Registry System: (R)-2-(phenylsulfinyl)ethanol(123299-91-2)

Safety Data

• Hazardous Substances Data: 123299-91-2(Hazardous Substances Data)

Upstream product

• 699-12-7 2-(phenylthio)ethanol 
• 930-69-8 sodium thiophenolate 
• 86428-23-1 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine 

Downstream Products

• 130513-97-2 (R)-2-((R)-Benzenesulfinyl)-propan-1-ol 
• 130513-96-1 (S)-2-((R)-Benzenesulfinyl)-propan-1-ol 
• 938-09-0 2-chloroethyl phenyl sulfone 
• 113493-62-2 (2-hydroxyethyl)(imino)(phenyl)-λ⁶-sulfanone 
• 143359-33-5 (R)-3-Phenyl-2-phenylsulfanyl-propan-1-ol 
• 699-12-7 2-(phenylthio)ethanol 
• 130514-33-9 (S)-2-((R)-Benzenesulfinyl)-pent-4-en-1-ol 
• 130514-34-0 (R)-2-((R)-Benzenesulfinyl)-pent-4-en-1-ol 
• 130514-31-7 (S)-2-((R)-Benzenesulfinyl)-3-phenyl-propan-1-ol 
• 130514-05-5 (R)-2-((R)-Benzenesulfinyl)-3-phenyl-propan-1-ol 
• 130514-32-8 (S)-2-((R)-Benzenesulfinyl)-decan-1-ol 
• 130514-06-6 (R)-2-((R)-Benzenesulfinyl)-decan-1-ol 

Relevant articles and documents

Peroxomolybdate supported on water soluble polymers as efficient catalysts for green and selective sulfoxidation in aqueous medium

Peroxomolybdenum(VI) species immobilized on linear water soluble polymers formulated as, [MoO(O2)2(sulfonate)]–PS [PS?=?poly(sodium vinyl sulfonate)] (PSMo) and[Mo2O2(O2)4(carboxylate)]–PA [PA?=?poly(sodium acrylate)](PAMo) served as efficient and recyclable catalysts for selective oxidation of organic sulfides to sulfoxide in water with 30% H2O2. The new polymer anchored complex, PSMo has been prepared by reacting H2MoO4 and 30% H2O2 with macromolecular ligand, poly(sodium vinyl sulfonate) and characterized by elemental analysis, spectral studies (FTIR, Raman, 13C NMR, 95Mo NMR, UV–vis), SEM, EDX and TGA-DTG analysis. The catalytic protocol effects clean and facile oxidation of a wide range of sulfides to afford pure sulfoxides with high TOF and excellent chemoselectivity at ambient temperature,with an easy work-up procedure. The catalysts can be regenerated in-situ and recycled at least up to ten consecutive reaction cycles without significant loss of activity and are amenable for ready scalability. The catalytic procedure thus provides an ecologically sustainable alternative as it involves water as solvent, H2O2 as green oxidant, a recyclable non-polluting catalyst, and is absolutely free from halide, organic co-solvent or co-catalyst. This is the first catalytic protocol for selective aqueous oxidation of sulfides using a catalytic system based on peroxometal species supported on water soluble polymers.

2,6-Dicarboxypyridinium chlorochromate: An efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides

2,6-Dicarboxypyridinium chlorochromate (2,6-DCPCC) was found to be an efficient reagent for the conversion of thiols to disulfides and sulfides to sulfoxides under neutral and anhydrous conditions in good to excellent yields. Selective oxidation of thiols in the presence of sulfides at room temperature is also observed with this reagent.

Catalytic oxidation of sulfides to sulfoxides by poly(4-vinyl pyridinium nitrate), silica sulfuric acid and ammonium bromide as a catalyst

A new catalytic procedure for the chemoselective oxidation of sulfides to sulfoxides was studied. A variety of aliphatic and aromatic sulfides were subjected to sulfoxidation by combining poly(4-vinyl pyridinium nitrate), silica sulfuric acid (SiO2-OSO3H), and catalytic amounts of ammonium bromide in CH2Cl2 in the presence of a few drops of water at room temperature. Excellent yields were obtained.

Immobilization of a vanadium complex onto functionalized nanoporous MCM-41 and its application as a catalyst for the solvent-free chemoselective oxidation of sulfide to sulfoxide

A complex moiety containing VO(IV) was anchored covalently into organic-modified Si-MCM-41 to prepare a new catalyst. The prepared materials were characterized using various techniques. Several types of aromatic and aliphatic sulfides were successfully oxidized to the corresponding sulfoxides in good to excellent yields using H2O2 in the presence of a catalytic amount of the catalyst under solvent-free conditions. The results showed that the OH groups of the various compounds such as 2,2-(phenylthio)ethanol and 2-(methylthio)ethanol remained intact under similar conditions. Meanwhile the catalyst was stable in the reaction system, and could be reused at least four times without significant loss of its activity and chemoselectivity.

Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing DMSO reductase

Preparation of enantiomerically enriched sulfoxides by an electrochemical enzymatic system utilizing DMSO reductase was studied. This system consists of a glassy carbon electrode as the working electrode, methyl viologen as the mediator and DMSO reductase

Preparation and characterization of oxovanadium(IV)-glycine imine immobilized on magnetic nanoparticles and its catalytic application for selective oxidation of sulfides to sulfoxides

A novel Fe3O4@VO (salen) complex was designed as an efficient and heterogeneous catalyst for selective oxidation of sulfides to sulfoxides using H2O2 at room temperature. The catalyst was characterized by techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD) analysis, Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), vibrating-sample magnetometry (VSM), and inductively coupled plasma optical emission spectrometry (ICP-OES) analysis. The simple preparation of the catalyst from commercially available materials, excellent chemoselectivity, easy separation of products, and straightforward recovery and reusability of the catalyst with unaltered activity make our procedure a green and practical method.

Covalent immobilization of Co complex on the surface of SBA-15: Green, novel and efficient catalyst for the oxidation of sulfides and synthesis of polyhydroquinoline derivatives in green condition

In this work, a green and novel catalyst was prepared through immobilization of cobalt complex on the surface of mesostructured SBA-15 and characterized by TGA, SEM, FT‐IR, EDX, ICP, BET and X-ray mapping analytical methods. This mesostructural material was used as an efficient and green interphase catalyst for the oxidation reactions and synthesis of polyhydroquinoline derivatives. All reactions were performed in short times and good yields. Moreover, the prepared catalyst could be used up to six runs without significant degradation in its catalytic activity or cobalt leaching.

Salen copper(II) complex heterogenized on mesoporous MCM-41 as nano-reactor catalyst for the selective oxidation of sulfides using urea hydrogen peroxide (UHP)

MCM-41 silica spheres were synthesized and functionalized with 3-aminopropyltriethoxysilane (3-APTES). The Schiff base has been derived from amino groups and 5-boromo salicylaldehyde, then a tetra dentate Cu(II)-Schiff base complex was prepared. This comp

Highly efficient selective oxidation of sulfides to sulfoxides by montmorillonite-immobilized metalloporphyrins in the presence of molecular oxygen

Highly efficient and selective oxidation of sulfides to sulfoxides with dioxygen catalyzed by cationic meso-tetrakis (1-methyl-4-pyridyl) (TM4PyP) metalloporphyrins immobilized into montmorillonite (MT) interlayer was achieved. Manganese (II) porphyrin (MnTM4PyP-MT) presented excellent activity for the oxidation of sulfides under ambient conditions. In the model oxidation, thioanisole was converted completely and the selectivity towards sulfoxide was up to 95%. This catalyst also showed high activity and selectivity for the most sulfides. The catalyst could be reused consecutively five times without significant loss of activity.

Diruthenium(II,III) tetracarboxylates catalyzed H2O2 oxygenation of organic sulfides

Diruthenium(II,III) tetracarboxylates, Ru2(OAc)4Cl (A), Ru2(esp)2Cl (B, esp = tetramethyl-1,3-benzenedipropionate) and Ru2(3-HB)4Cl (C, 3-HB = 3-hydroxybenzoate) were investigated for activating hydrogen peroxide in organic sulfide oxygenation. The speciation of the substrate and potential products, sulfoxide and sulfone, were investigated for each catalyst. With methyl phenyl sulfide as the substrate, A simultaneously produces sulfoxide and sulfone, B yields the highest turnover with complete conversion to sulfoxide at 6 min before sulfone appears, and C facilitates complete conversion to sulfoxide in 20 min but little subsequent conversion to sulfone. The dependence of the initial reaction rate on catalyst and H2O2 concentrations were investigated. A small set of other sulfides were subjected to catalytic reactions with C, and all reactions resulted in near quantitative conversion. Finally, the sulfide oxygenation activity and stability towards hydrogen peroxide of the diphosphonate complex Na4[Ru2(hedp)2(H2O)Cl] (D, hedp = 1-hydroxyethylidenediphosphonate) was investigated, and D was found to be an effective catalyst, which retains its activity over an extended period of time due to its robustness at the (III,III) oxidation state.

Efficient oxidation of sulfides to the sulfoxides using zirconium (IV) chloride, sodium nitrite and catalytic amounts of bromide ion as a novel oxidizing media

Chemo and homoselective catalytic oxidation of sulfides has been developed. A variety of aliphatic and aromatic sulfides are subjected to the sulfoxidation reaction using ZrCl4, NaNO2 and catalytic amounts of KBr or NaBr in the prese

Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions

Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]

Cu–citric acid metal–organic framework: Synthesis, characterization and catalytic application in Suzuki–Miyaura cross-coupling reaction and oxidation of sulfides

Citric acid with three carboxylic groups was used as an outstanding chelating agent was utilized for the preparation of Cu–citric acid metal–organic framework (Cu–CA–MOF). The prepared MOF was characterized by FT-IR, XRD, EDS, AAS, SEM, WDX and BET analysis. N2 adsorption–desorption isotherms indicated acceptable BET surface area for Cu–CA–MOF. SEM images were shown that Cu–CA–MOF has geometric polyhedral shapes. Also, catalytic activity of Cu–CA–MOF successfully examined for the Suzuki–Miyaura cross-coupling reaction and chemoselective oxidation of sulfides to sulfoxides.