5056-07-5

Basic information

• Product Name: (S)-(-)-METHYL P-TOLYL SULFOXIDE
• Synonyms: (S)-(-)-METHYL P-TOLYL SULFOXIDE;(S)-(-)-METHYL P-TOLYL SULFOXIDE, 99% (9;(S)-Methyl 4-tolyl sulfoxide;(S)-Methyl p-methylphenyl sulfoxide;(S)-p-Methylphenyl methyl sulfoxide;(S)-p-Tolyl methyl sulfoxide;1-Methyl-4-[(S)-methylsulfinyl]benzene;S-(4-Methylphenyl) methyl sulfoxide
• CAS NO: 5056-07-5
• Molecular Formula: C₈H₁₀OS
• Molecular Weight: 154.23
• Product Categories: Chiral Compound;Chiral Building Blocks;Organic Building Blocks;Sulfoxides
• Mol File: 5056-07-5.mol
• Article Data: 176

Chemical Properties

• Melting Point: 75-77 °C(lit.)
• Boiling Point: 282.403°C at 760 mmHg
• Flash Point: 124.593°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.59
• BRN: 2324696
• CAS DataBase Reference: (S)-(-)-METHYL P-TOLYL SULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-METHYL P-TOLYL SULFOXIDE(5056-07-5)
• EPA Substance Registry System: (S)-(-)-METHYL P-TOLYL SULFOXIDE(5056-07-5)

Safety Data

• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 5056-07-5(Hazardous Substances Data)

Usage

Description

(S)-(-)-METHYL P-TOLYL SULFOXIDE is an organic compound that serves as a nucleophilic reagent in various chemical reactions. It is characterized by its chiral center, which gives it optical activity, and its sulfoxide functional group, which provides unique reactivity in organic synthesis.

Uses

Used in Pharmaceutical Industry:
(S)-(-)-METHYL P-TOLYL SULFOXIDE is used as a nucleophilic reagent for the synthesis of optically active β-disulfoxides. This application is crucial for the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the production of chiral drugs with specific biological activities.
Used in Organic Synthesis:
(S)-(-)-METHYL P-TOLYL SULFOXIDE is used as a nucleophilic reagent for the preparation of α-substituted N-hydroxylamines by treating with nitrones. This reaction is important in organic synthesis, as N-hydroxylamines are versatile intermediates for the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds.
Used in Carbohydrate Chemistry:
(S)-(-)-METHYL P-TOLYL SULFOXIDE is used as a nucleophilic reagent for the one-carbon homologation of 2,3-O-isopropylidene-L-glyceraldehyde to produce 2-O-benzyl-3,4-O-isopropylidene-L-erythrose. This reaction is significant in carbohydrate chemistry, as it allows for the synthesis of modified carbohydrates with potential applications in the development of new drugs, vaccines, and other bioactive compounds.

InChI:InChI=1/C8H10OS/c1-7-3-5-8(6-4-7)10(2)9/h3-6H,1-2H3/t10-/m1/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 52154-24-2 (R)-p-tolylsulfinylacetophenone 
• 623-13-2 4-methylphenyl methylsulfide 
• 75-16-1 methylmagnesium bromide 
• 142635-30-1 (4S)-4-benzyl-3-<(S)-p-tolylsulfinyl>-2-isoxazolidinone 
• 31350-91-1 (R)-chloromethyl p-tolyl sulfoxide 
• 52720-03-3 (R)-imino(methyl)(p-tolyl)-λ⁶-sulfanone 
• 91796-57-5 4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 134311-28-7 (+)-(1S,2R)-trans-2-phenylcyclohexyl (S)-methanesulfinate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 135802-77-6 (S_S)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl methanesulfinate 
• 917-54-4 methyllithium 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 114026-76-5 (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane 

Downstream Products

• 113002-37-2 5-Methyl-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 104891-35-2 (S)-(-)-1-chloro-3-<(4-methylphenyl)sulphinyl>propan-2-one 
• 267241-54-3 (-)-(S_S)-1-(p-tolylsulfinyl)-4-(1,3-dioxolane)-2-oxo-heptane 
• 113002-31-6 (3S)-(R_S)-3-benzyloxymethyl-3,4-dihydro-6-methyl-5-p-tolylsulfinyl-2H-pyran 
• 113002-40-7 [(S)-6-(3-Methyl-butyl)-5-((S)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-41-8 [(R)-6-(3-Methyl-butyl)-5-((S)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-27-0 [(R)-6-Methyl-5-((R)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-27-0 [(S)-6-Methyl-5-((S)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-35-0 [(R)-6-Methyl-5-((S)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-30-5 (R)-1-Methyl-7-((S)-toluene-4-sulfinyl)-2,6-dioxa-bicyclo[2.2.2]octane 
• 113002-30-5 (S)-1-Methyl-7-((S)-toluene-4-sulfinyl)-2,6-dioxa-bicyclo[2.2.2]octane 
• 113002-38-3 1-(2,2-Dimethyl-[1,3]dioxan-5-yl)-6-methyl-2-((R)-toluene-4-sulfinyl)-heptan-3-one 
• 113002-39-4 1-Hydroxy-2-hydroxymethyl-8-methyl-4-((R)-toluene-4-sulfinyl)-nonan-5-one 
• 113002-33-8 (S)-1-(3-Methyl-butyl)-7-((S)-toluene-4-sulfinyl)-2,6-dioxa-bicyclo[2.2.2]octane 

Relevant articles and documents

Diketobile acids as new hosts in solid-state enantioselective resolutions

New diketobile acid derivatives have been evaluated as hosts in the resolution of aryl methyl sulfoxides. The guest molecules are linked to the host ones via hydrogen bonds with the SO group. The 3,6-diketo derivative is also effective for the resolution of γ-lactames. Copyright

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.

Enzymatic kinetic resolution of chiral sulfoxides-an enantiocomplementary approach

A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.