1519-39-7

Basic information

• Product Name: (R)-(+)-Methyl p-tolyl sulfoxide
• Synonyms: (R)-(+)-METHYL P-TOLYL SULFOXIDE;(R)-methyl4-methylphenylsulfoxide;1-Methanesulfinyl-4-methyl-benzene;(R)-1-Methyl-4-(Methylsulfinyl)benzene;(R)-(+)-Methyl p-tolyl sulfoxide 99%
• CAS NO: 1519-39-7
• Molecular Formula: C₈H₁₀OS
• Molecular Weight: 154.23
• Product Categories: Chiral Compound;Chiral Building Blocks;Organic Building Blocks;Sulfoxides
• Mol File: 1519-39-7.mol
• Article Data: 186

Chemical Properties

• Melting Point: 73-75 °C(lit.)
• Boiling Point: 247.62°C (rough estimate)
• Flash Point: 124.6 °C
• Appearance: /
• Density: 1.1125 (rough estimate)
• Vapor Pressure: 0.00574mmHg at 25°C
• Refractive Index: 1.5780 (estimate)
• BRN: 2040677
• CAS DataBase Reference: (R)-(+)-Methyl p-tolyl sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-Methyl p-tolyl sulfoxide(1519-39-7)
• EPA Substance Registry System: (R)-(+)-Methyl p-tolyl sulfoxide(1519-39-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 1519-39-7(Hazardous Substances Data)

Usage

Description

(R)-(+)-Methyl p-tolyl sulfoxide is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds, including (R)-lasiodiplodin. It is characterized by its ability to undergo addition reactions with nitrones to form optically active a-substituted N-hydroxylamines and reacts with O-mesitylsulfonylhydroxylamine (MSH) to form (-)-(R)-S-methyl-S-p-tolylsulfoximine.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-Methyl p-tolyl sulfoxide is used as a key intermediate for the synthesis of (R)-(+)-methyl 3,5-dimethoxy-6-[8-oxo-9-(p-tolylsulfinyl) nonyl] benzoate, which is an essential component in the production of (R)-lasiodiplodin. (R)-(+)-Methyl p-tolyl sulfoxide has potential applications in the development of new drugs and therapies.
Used in Chemical Synthesis:
(R)-(+)-Methyl p-tolyl sulfoxide is used as a reactant in the formation of optically active a-substituted N-hydroxylamines through addition reactions with nitrones. These N-hydroxylamines can be further utilized in the synthesis of various pharmaceutical compounds and other specialty chemicals.
Used in Research and Development:
(R)-(+)-Methyl p-tolyl sulfoxide is also used in research and development for the study of its chemical properties and potential applications in the synthesis of novel compounds. Its reaction with O-mesitylsulfonylhydroxylamine (MSH) to form (-)-(R)-S-methyl-S-p-tolylsulfoximine is an example of its utility in creating new chemical entities for further investigation and potential commercialization.

InChI:InChI=1/C8H10OS/c1-7-3-5-8(6-4-7)10(2)9/h3-6H,1-2H3/t10-/m0/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 623-13-2 4-methylphenyl methylsulfide 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 75-16-1 methylmagnesium bromide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 135802-77-6 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl-(-)-<(S)S>-methanesulfinate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 74-88-4 methyl iodide 
• 917-54-4 methyllithium 
• 161691-32-3 (S)-2-Phenyl-1-((S)-toluene-4-sulfinyl)-aziridine 
• 172617-59-3 (S)-2-Naphthalen-1-yl-1-((S)-toluene-4-sulfinyl)-aziridine 
• 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 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 

Downstream Products

• 20520-50-7 (R)-S-methyl-S-(4-tolyl)-N-(p-tolylsulfonyl)sulfoximine 
• 20414-85-1 (R)-imino(methyl)(p-tolyl)-λ⁶-sulfanone 
• 50789-50-9 (2S,R_S)-2-(anilino)-2-phenylethyl p-tolyl sulfoxide 
• 26910-35-0 (+)-bromomethyl p-tolyl sulfoxide 
• 105984-81-4 (R_S)-3,3-difluoro-1-<(4-methylphenyl)sulphinyl>-4,4,4-trifluoro-butane-2,2-diol 
• 104891-11-4 3-Bromo-3-methyl-1-((R)-toluene-4-sulfinyl)-butan-2-one 
• 133043-10-4 5-oxo-6-(p-tolylsulfinyl)hexanoic acid 
• 121411-13-0 (4-Methoxy-phenyl)-[(R)-1-(4-nitro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-amine 
• 121411-14-1 (4-Methoxy-phenyl)-[(S)-1-(4-nitro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-amine 
• 124687-90-7 [(R)-1-Furan-2-yl-2-((R)-toluene-4-sulfinyl)-ethyl]-phenyl-amine 
• 124687-74-7 [(S)-1-Furan-2-yl-2-((R)-toluene-4-sulfinyl)-ethyl]-phenyl-amine 
• 124992-51-4 2-<(4-methylphenyl)sulfinyl>-1-(2-pyridyl)ethanone 
• 141362-04-1 1,1-Diphenyl-2-((R)-toluene-4-sulfinyl)-ethanol 
• 85617-03-4 1-((R)-Toluene-4-sulfinyl)-undecan-2-ol 

Relevant articles and documents

Nonlinear Effects in Asymmetric Synthesis. Examples in Asymmetric Oxidations and Aldolization Reactions

It has been shown in three experiments that there is a strong departure from the linear relationship usually assumed between the enantiomeric excess of a chiral auxiliary and the extent of the asymmetric synthesis.This gives useful information on the reac

Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts

Nonlinear effects (NLEs) have been used as a new tool to characterize the various modifications of a chiral titanium complex used in stoichiometric or catalytic mode in asymmetric sulfoxidation by cumyl hydroperoxide. Spectacular changes from (+)- to (-)-NLEs were observed for minor modifications of the experimental conditions.

Kinetic resolution of sulfoxides catalyzed by chiral titanium-binaphthol complex

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Optically active polyoxotungstates bearing chiral organophosphonate substituents

Divacant Keggin-type polyoxotungstates [γ-XW10O 36]8-with X = Si or Ge, were functionalized with chiral phosphoryl groups. The hybrid compounds [(RPO)2(γ-XW 10O36)]4- with R = N-

Asymmetric oxidation with furylhydroperoxides

Chiral sulfoxides are accessible with very satisfactory enantiomeric excesses through a modified Sharpless procedure, based on the employment of furylhydroperoxides. Racemic hydroperoxides are found to undergo a kinetic resolution in the course of the asy

Biotransformation of organic sulfides. Predictive active site models for sulfoxidation catalysed by 2,5-diketocamphane 1,2-monooxygenase and 3,6- diketocamphane 1,6-monooxygenase, enantiocomplementary enzymes from Pseudomonas putida NCIMB 10007

Growth of the bacterium Pseudomonas putida NCIMB 10007 on racemic camphor induces two enantiocomplementary diketocamphane monooxygenase isofunctional enzymes (isozymes) both able to catalyse electrophilic biooxidation of a wide range of prochiral sulfoxides to the corresponding chiral sulfoxides. Active site models to explain and predict the stereoselectivity of the sulfoxidations catalysed by both isozymes are proposed. The models are based on restrictive space descriptors derived from the optimised outcomes obtained with 23 different phenyl alkyl, benzyl alkyl, methyl alkyl and ethyl alkyl sulfides: consistency was maximised by using the same enzyme preparations throughout. The models, which are consistent with the recognised stereoselectivities of diketocamphane monooxygenase catalysed nucleophilic biooxidations of ketones to lactones, are the first to provide insight into the active site topography of FMN plus NADH-dependent Baeyer- Villiger monooxygenases. In addition, they are unique in providing a direct comparison of the active sites of two enantiocomplimentary isofunctional proteins that have evolved in the same cell line.

Acid promoted enantioselective oxygen-atom transfer from N-alkyl binaphthyl-derived oxaziridines onto sulfides

Acid-promoted asymmetric sulfoxidations of prochiral sulfides using binaphthyl-derived oxaziridines have been studied. The reactions of dialkyl or aryl-alkyl sulfides gave good yields of the corresponding sulfoxides with enantiopurities ranging from 20% to 80%. The influence of temperature and strength of the acid catalyst on enantioselectivity was studied. The absolute configuration of the resulting major enantiomer varied with the structure of the sulfide.

Asymmetric oxidation of sulfide to sulfoxides on Ti-containing mesoporous silica catalysts with hydrogen peroxide in the presence of optically active tartaric acid

On Ti-containing MCM-41 prepared by a template ion-exchange method, sulfide could be asymmetrically oxidized to sulfoxides in the presence of optically active tartaric acid (54% yield and 30% ee). The oxidation was composed of the asymmetric induction to sulfoxides and the subsequent kinetic resolution of sulfoxides.

Kinetic resolution of racemic sulfoxides by a modified Sharpless procedure

Kinetic resolution of racemic sulfoxides is achieved by enantioselective oxidation to sulfones under Sharpless-type conditions.

Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases

We report on the development of high-throughput fluorogenic assay that can streamline directed evolution of enantioselective sulfoxide reductases. As a model, methionine sulfoxide reductase A (MsrA) has been evolved to expand its limited substrate scope. The resulting mutant MsrA can resolve a range of new challenging racemic sulfoxides with high efficiency including the pharmaceutically relevant albendazole sulfoxide. The simplicity and the level of throughput make this method also suitable for the screening of metagenomic libraries in future for the discovery of new enzymes with similar reactivities.

Chemoenzymatic Deracemization of Chiral Sulfoxides

The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.