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1193-82-4

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1193-82-4 Usage

Chemical Properties

white crystalline low melting mass

Uses

Methyl phenyl sulfoxide has been used in the synthesis of:isotopically labelled 1, 3-dithiane, a useful labeled synthonnelfinavir, potent HIV-protease inhibitorsulfoximines and in studies on solvent-water partitioning

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2847, 1985 DOI: 10.1021/jo00216a007Tetrahedron Letters, 22, p. 4591, 1981 DOI: 10.1016/S0040-4039(01)82989-0

General Description

(R)-methyl phenyl sulfoxide is an important pharmaceutical intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 1193-82-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 3 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1193-82:
(6*1)+(5*1)+(4*9)+(3*3)+(2*8)+(1*2)=74
74 % 10 = 4
So 1193-82-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H8OS/c1-9(8)7-5-3-2-4-6-7/h2-6H,1H3

1193-82-4 Well-known Company Product Price

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  • TCI America

  • (M1148)  Methyl Phenyl Sulfoxide  >98.0%(GC)

  • 1193-82-4

  • 5g

  • 425.00CNY

  • Detail
  • TCI America

  • (M1148)  Methyl Phenyl Sulfoxide  >98.0%(GC)

  • 1193-82-4

  • 25g

  • 1,160.00CNY

  • Detail
  • Alfa Aesar

  • (A15009)  Methyl phenyl sulfoxide, 98+%   

  • 1193-82-4

  • 5g

  • 315.0CNY

  • Detail
  • Alfa Aesar

  • (A15009)  Methyl phenyl sulfoxide, 98+%   

  • 1193-82-4

  • 25g

  • 1249.0CNY

  • Detail
  • Alfa Aesar

  • (A15009)  Methyl phenyl sulfoxide, 98+%   

  • 1193-82-4

  • 100g

  • 4535.0CNY

  • Detail
  • Aldrich

  • (261696)  Methylphenylsulfoxide  ≥97%

  • 1193-82-4

  • 261696-5G

  • 428.22CNY

  • Detail
  • Aldrich

  • (261696)  Methylphenylsulfoxide  ≥97%

  • 1193-82-4

  • 261696-25G

  • 1,614.60CNY

  • Detail

1193-82-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name METHYL PHENYL SULFOXIDE

1.2 Other means of identification

Product number -
Other names methylsulfinylbenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1193-82-4 SDS

1193-82-4Relevant articles and documents

Template Effects of a Clay-Chelate Adduct on the Asymmetric Oxidation of Alkyl Phenyl Sulphide by Sodium Metaperiodate

Yamagishi, Akihiko

, p. 290 - 291 (1986)

Cyclohexyl phenyl sulphide adsorbed by Δ-tris(1,10-phenanthroline)nickel(II)-montmorillonite was oxidized by sodium metaperiodate at 25 deg C in water to give (S)-cyclohexyl phenyl sulphoxide with an optical purity of 78percent.

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Davis,F.A. et al.

, p. 5171 - 5174 (1978)

-

Effects of the environment on microperoxidase-11 and on its catalytic activity in oxidation of organic sulfides to sulfoxides

Kadnikova, Ekaterina N.,Kostic, Nenad M.

, p. 2600 - 2608 (2003)

Microperoxidase-11 (MP-11, also known as heme undecapeptide of cytochrome c) was immobilized by encapsulation into sol-gel silica glass and by physisorption, chemisorption, and covalent attachment to silica gel. We then compared these species with one ano

Catalytic Asymmetric Oxidation of Sulfides to Sulfoxides with tert-Butyl Hydroperoxide Using Binaphthol as a Chiral Auxiliary

Komatsu, Naoki,Hashizume, Masaya,Sugita, Toshio,Uemura, Sakae

, p. 4529 - 4533 (1993)

The asymmetric oxidation of sulfides to chiral sulfoxides in moderate yield with tert-butyl hydroperoxide (TBHP) was catalyzed very effectively by a titanium complex produced in situ from a titanium alkoxide and a chiral binaphthol.The highest enantioselectivities (up to 96percent ee) were obtained with commercial aqueous 70percent TBHP under atmospheric conditions at 25 deg C with 2.5 mol percent of the catalyst.The presence of more than 1.0 mol equiv of water relative to sulfide was essential for the oxidation, and it was found that the water was necessary not only to produce an effective catalyst for the highly enantioselective oxidation but also to maintain the catalytic activity of the titanium-binaphthol complex for a longer time.The nature of the solvent had a remarkable effect upon the ee of the sulfoxide.Carbon tetrachloride was proven to be the solvent of choice; the use of other chlorinated solvents resulted in low enantioselectivity.A moderate level of asymmetric amplification was observed in this catalytic system.From a mechanistic standpoint, it was revealed that the initial asymmetric oxidation to the chiral sulfoxide (ca. 50percent ee) is followed by the kinetic resolution of the sulfoxide; that is, the titanium-binaphthol complex catalyzes not only the asymmetric oxidation but also the subsequent kinetic resolution.

Ni(II) and V(IV) Schiff base complexes derived from 2,2′-dimethylpropandiamine: the crystal structure, electrochemical properties and catalytic activities in oxidation of sulfides

Rayati, Saeed,Khodaei, Elham,Jafarian, Majid,Bahrami, Arezo,Wojtczak, Andrzej,Kozakiewicz, Anna

, p. 1424 - 1437 (2017)

Tetradentate Schiff base (H2L) derived from 2,2′-dimethylpropandiamine and its nickel(II) and oxo-vanadium(IV) complexes (NiL, VOL) have been prepared and characterized. The crystal structure of NiL has been determined. The reported structure c

Direct evidence for oxygen-atom exchange between nonheme oxoiron(IV) complexes and isotopically labeled water

Seo, Mi Sook,In, Jun-Hee,Kim, Sun Ok,Oh, Na Young,Hong, Jongki,Kim, Jinheung,Que Jr., Lawrence,Nam, Wonwoo

, p. 2417 - 2420 (2004)

Rates of exchange: Evidence that non-heme oxoiron(IV) complexes exchange their oxygen atoms with H218O was obtained for the first time, by monitoring electrospray ionization mass spectral changes of the oxoiron(IV) species. The oxyge

Chiral ionic liquids for catalytic enantioselective sulfide oxidation

Bigi, Franca,Nimal Gunaratne,Quarantelli, Carla,Seddon, Kenneth R.

, p. 685 - 687 (2011)

A new class of catalytic ionic liquids, containing chiral tungstate(VI) anions, gives enantiomeric excesses up to 96% for sulfide oxidation to sulfoxides.

α-Fluorination of Sulfoxides Bearing α-Hydrogens by Molecular Fluorine. A Novel Method for the Synthesis of α-Fluorosulfones

Chiba, Jun,Sugihara, Takumichi,Kaneko, Chikara

, p. 581 - 582 (1995)

Direct formation of α-fluorosulfones from sulfoxides bearing α-hydrogens merely by reacting molecular fluorine (5percent F2/N2) is reported and a possible mechanism for this novel α-fluorination reaction is proposed.

New metal complexes supported on Fe3O4 magnetic nanoparticles as recoverable catalysts for selective oxidation of sulfides to sulfoxides

Hajjami, Maryam,Kolivand, Somaye

, p. 282 - 288 (2016)

Fe3O4 nanoparticles were coated with aminopropyltriethoxysilane and subsequently reacted with isatin to obtain imine-bonded Fe3O4 nanoparticles. The addition of ZrOCl2·8H2O or CuCl2 led to the formation of complexes of Zr(IV)/isatin@Fe3O4 or Cu (II)/isatin@Fe3O4 as new magnetically separable catalysts. The synthesized catalysts were characterized using various techniques. These catalysts are shown to be efficient for chemo-selective oxidation of sulfides to sulfoxides using hydrogen peroxide as oxidative agent. This system has many advantages, such as excellent level of reusability of magnetic catalysts, high yields, simplicity of separation of catalysts using an external magnet, environmental benignity and ease of handling.

On the nature of the chain-extending species in organolithium initiated stereospecific reagent-controlled homologation reactions using α-chloroalkyl aryl sulfoxides

Hoyt, Amanda L.,Blakemore, Paul R.

, p. 2980 - 2982 (2015)

The reaction of an organolithium with an α-chloroalkyl aryl sulfoxide ostensibly generates an α-chloroalkyllithium by sulfoxide-lithium exchange, but the actual identity of the chain-extending species in chlorosulfoxide-based StReCH reactions is not certain. To explore this issue, racemic 2-cyclohexyl (4R?,5R?)-4,5-diphenyl-1,3,2-dioxaborolane was homologated by treatment with scalemic (S)-chloromethyl phenyl sulfoxide and n-BuLi (THF, -78 °C). The reaction proceeded without a detectable level of kinetic resolution, a finding consistent with chloromethyllithium being the active chain-extending species rather than a chiral sulfurane intermediate.

Enantioselective oxidation of thioanisole with an alcohol oxidase/peroxidase bienzymatic system

Pezzotti, Fabio,Therisod, Michel

, p. 701 - 704 (2007)

Optimization of a new bienzymatic couple alcohol oxidase/peroxidase for the asymmetric oxidation of thioanisole was realized. The main advantages in the application of this system is the use of inexpensive and easily available enzymes and substrates, perm

Conversion of myoglobin into a peroxygenease: A catalytic intermediate of sulfoxidation and epoxidation by the F43H/H64L mutant

Ozaki,Matsui,Watanabe

, p. 6666 - 6667 (1997)

-

Highly enantioselective sulfoxidation with vanadium catalysts of Schiff bases derived from bromo- and iodo-functionalized hydroxynaphthaldehydes

Wang, Ying,Wang, Mei,Wang, Yu,Wang, Xiuna,Wang, Lin,Sun, Licheng

, p. 177 - 181 (2010)

Two series of chiral Schiff bases, 4a-e and 5a-e, prepared from the condensation of the mono-, di-, tribromohydroxynaphthaldehyde or monoiodohydroxynaphthaldehyde with chiral amino alcohols, were used in combination with VO(acac)2 for the asymmetric oxidation of aryl methyl sulfides using H2O2 as terminal oxidant. Among these Schiff bases, dibromo-functionalized 4d and iodo-functionalized 5e gave high yields (91-93%) with good enantioselectivities (80-82% ee) for the oxidation of thioanisole in dichloromethane. The asymmetric oxidation of thioanisole in toluene using these Schiff bases gave methyl phenyl sulfoxide in satisfactory isolated yields (48-62%) with high enantioselectivities (91-94% ee), which were further improved by a modified procedure with the ee value up to 98% in 62% yield. The oxidations of other aryl methyl sulfides in toluene with dibromo- and iodo-functionalized Schiff bases 5d and 5e as ligands using the modified procedure afforded the corresponding sulfoxides in 55-67% isolated yields with 95-99% ee.

-

Manya et al.

, p. 467,475 (1970)

-

-

Landini et al.

, p. 7168,7169 - 7171, 7173 (1970)

-

C3-symmetric Ti(IV) triphenolate amino complexes as sulfoxidation catalysts with aqueous hydrogen peroxide

Mba, Myriam,Prins, Leonard J.,Licini, Giulia

, p. 21 - 24 (2007)

(Chemical Equation Presented) The Ti(IV) complex 2c bearing a C 3-symmetric triphenolate amine ligand is an air and moisture tolerant complex that efficiently catalyzes sulfoxidation reactions at room temperature without previous activation (catalyst loading down to 0.01%, TONs up to 8000, TOFs up to 1700 h-1, quantitative yields). Reactions were performed with aqueous hydrogen peroxide as oxidant, which adds value to the methodology from the environmental viewpoint.

-

Oae,S. et al.

, p. 648 - 649 (1973)

-

Guest dependent inversion of enantiomeric recognition in dehydrocholic acid host-guest enclathration

Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Perrone, Daniela

, p. 1194 - 1196 (2007)

A guest dependent inversion of enantiomeric recognition operated by the host dehydrocholic acid on a second guest is observed during host-guest dehydrocholic acid-sulfoxide assembly formation.

Facile synthesis of a 3D flower-like SiO2-MOF architecture with copper oxide as a copper source for enantioselective capture

Li, Xinglin,Gao, Yu,Wang, Cuijie,Cui, Jiting,Yu, Ajuan,Zhang, Shusheng

, p. 16123 - 16126 (2019)

A facile self-template synthetic approach for the facile synthesis of a 3D flower-like SiO2-CuLBH architecture with copper oxide as a copper source has been demonstrated. The resulting composite as a sorbent showed a certain selective separation capability for phenyl methyl sulfoxide enantiomers (PMS) with an enantiomeric excess (ee) value of 31%.

Enantiopure 24-armed dendritic polyoxometalates: Synthesis and evaluation as recoverable catalysts for asymmetric sulfide oxidation

Jahier, Claire,Touzani, Rachid,El Kadiri, Sghir,Nlate, Sylvain

, p. 81 - 86 (2016)

Enantiopure 24-armed dendritic polyoxometalate (DENDRI-POM) hybrids were prepared by ionic coupling of enantiopure 8-armed n-propyl dendritic ammoniums with a catalytically active peroxophosphotungstate trianion {PO4[WO(O2)2]4}3-. The catalytic properties of these DENDRI-POM hybrids were evaluated in the oxidation of thioanisole as a model reaction and compared to those of the 12-armed n-propyl analogous previously reported in our group. Up to 10% enantiomeric excess (ee) was obtained, indicating a negative effect on the reaction rate and the enantioselectivity, whereas the selectivity to the chiral sulfoxide versus sulfone was improved. This study AIDS understanding of how the structure and size of the dendritic wedge around the POM can influence its catalytic properties, especially regarding enantioselectivity. Four catalytic cycles were performed without any obvious change in the activity, selectivity and enantioselectivity.

Catalytic asymmetric oxidation of sulfides to sulfoxides using R-(+)-binaphthol

Komatsu, Naoki,Nishibayashi, Yoshiaki,Sugita, Toshio,Uemura, Sakae

, p. 5391 - 5394 (1992)

An asymmetric oxidation system using R-(+)-binaphthol as a chiral auxiliary catalyzes the oxidation of sulfides to chiral sulfoxides in good enantiomeric excess ( up to 73% e.e. ) and in a high chemical yield.

Modeling the cis-Oxo-Labile binding site motif of non-heme iron oxygenases: Water exchange and oxidation reactivity of a non-heme iron(IV)-Oxo compound bearing a tripodal tetradentate ligand

Company, Anna,Prat, Irene,Frisch, Jonathan R.,Mas-Balleste, Dr Ruben,Gueell, Mireia,Juhasz, Gergely,Ribas, Xavi,Muenck, Dr Eckard,Luis, Josep M.,Que Jr., Lawrence,Costas, Miquel

, p. 1622 - 1634 (2011)

The spectroscopic and chemical characterization of a new synthetic non-heme iron(IV)-oxo species [FeIV(O)(Me,HPytacn)(S)] 2+ (2, Me,HPytacn=1-(2′-pyridylmethyl)-4,7-dimethyl- 1,4,7-triazacyclononane, S=CH3CN or H2O) is described. Complex 2 was prepared by reaction of [FeII(CF3SO 3)2(Me,HPytacn)] (1) with peracetic acid. Complex 2 bears a tetradentate N4 ligand that leaves two cis sites available for binding an oxo group and a second external ligand but, unlike the related iron(IV)-oxo species with tetradentate ligands, it is remarkably stable at room temperature (t1/2>2a h at 288a K). Its ability to exchange the oxygen atom of the oxo ligand with water has been analyzed in detail by means of kinetic studies, and a mechanism is proposed on the basis of DFT calculations. Hydrogen-atom abstraction from C-H bonds and oxygen-atom transfer to sulfides by 2 have also been studied. Despite its thermal stability, 2 proves to be a very powerful oxidant that is capable of breaking the strong C-H bond of cyclohexane (bond dissociation energy=99.3a kcala mol-1). A powerful oxidant: A non-heme oxo-iron(IV) complex (see picture), containing a labile site cis to the terminal oxo group, has been prepared and characterized. The complex is unusually stable (t1/2>2a h at 288a K). Water exchange, oxo transfer, and Ha abstraction reactions have been studied. Despite its thermal stability, the complex is a very powerful oxidant.

Oxidation with mercury(II) oxide-iodine reagent: Selective oxidation of sulfides to sulfoxides

Orito,Hatakeyama,Takeo,Suginome

, p. 1357 - 1358 (1995)

A new method for selective oxidation of sulfides to sulfoxides with mercury(II) oxide-iodine reagent is reported.

Constraining titanium tartrate in the interlayer space of layered double hydroxides induces enantioselectivity

Shi, Huimin,Yu, Chenguang,He, Jing

, p. 79 - 87 (2010)

Kagan-Medona and Sharpless titanium tartrate complexes (Ti(IV)TAm, subscript m represents the coordination ratio of l-tartaric acid to the Ti center in the complex) have been intercalated into the interlayer of layered double hydroxides (LDHs) by anionic exchange method using Mg/Al-CO3 LDH as the precursor. Titanium tartrate-intercalated LDHs (designated Mg/Al-Ti(IV)TAm LDHs) with varied interlayer spacing were produced by tuning the area unit charge (Ac) of the brucite-like layer from 0.24 to 0.44 nm2. The interlayer spacing decreases from 1.87 to 1.44 nm with the increase in Ac. The interlayer titanium tartrate anions are present in an interdigitated bilayer arrangement. The bidimensional interlayer space can be swollen, and thus accommodates the reactants in the interlayer. The titanium tartrate complex constrained in the LDH interlayer region shows enhanced asymmetric induction in the heterogeneous sulfoxidation of pro-chiral methyl phenyl sulfide.

Chemoselective and efficient oxidation of sulfides to sulfoxides mediated by trimethylsilyl chloride and superoxide via a trimethylsilylperoxy radical

Chen, Yao-Jung,Huang, Yu-Ping

, p. 5233 - 5236 (2000)

Chemoselective and efficient oxidation of various sulfides were mediated by Me3SiCl and KO2 in dry acetonitrile at -15°C to afford corresponding sulfoxides in excellent yields without any interference in the presence of ketone, olefin, ether and hydroxyl functionalities and without further oxidation to the sulfones. A trimethylsilylperoxy radical generated in situ from this new process is proposed. (C) 2000 Elsevier Science Ltd.

Tungstate supported on magnetic ionic liquid-modi?ed graphene oxide as an efficient and recyclable catalyst for the selective oxidation of sulfides

Dabiri, Minoo,Tavil, Hassan Esmaielie,Lehi, Noushin Farajinia,Movahed, Siyavash Kazemi,Mnachekanian Salmasi, Aram,Souri, Sepideh

, (2021/11/30)

An effective and recyclable catalyst based on tungstate ion immobilization on magnetic ionic liquid modified graphene oxide (WO4@Fe3O4/GO-IL) has been synthesized in this research. The catalyst was characterized by various

Two enantiocomplementary Baeyer-Villiger monooxygenases newly identified for asymmetric oxyfunctionalization of thioether

Liu, Yafei,Ni, Ye,Wei, Shiyu,Xu, Guochao,Zhou, Jieyu

, (2021/08/19)

Two enantiocomplementary Baeyer-Villiger monooxygenases RaBVMO and AmBVMO were identified by genome mining for the asymmetric sulfoxidation. Both recombinant BVMOs have optimal pH of 9.0 and temperature of 35 °C. The half-lives of RaBVMO and AmBVMO at 30 °C were 24.4 and 24.6 h. RaBVMO and AmBVMO exhibited broad substrate spectrum and could catalyze the oxidization of various compounds including fatty ketones, cyclic ketones, and thioethers. Kinetic parameters analysis revealed that both RaBVMO and AmBVMO displayed higher catalytic efficiency toward thioanisole than cyclohexanone. As much as 50 mM thioanisole could be completely oxidized by AmBVMO and RaBVMO with 99% (R) and 95% (S), respectively. Molecular docking analysis further provides evidence for the complementary enantioselectivity of RaBVMO and AmBVMO. Our results demonstrate the potential application of the two novel BVMOs in asymmetric synthesis of sulfoxides.

Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones

Li, Jin-Heng,Li, Yang,Sun, Qing,Xue, Qi,Zhang, Ting-Ting

supporting information, p. 10314 - 10318 (2021/12/17)

A practical and eco-friendly method for the controllable aerobic oxygenation of sulfides by electrochemical catalysis was developed. The switchable preparation of sulfoxides and sulfones was effectively controlled by reaction time, in which both molecular oxygen and water can be used as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope and excellent site selectivity and is successfully applied to the modification of some sulfide-containing pharmaceuticals and their derivatives. This journal is

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