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

Uses

(S)-(-)-Methyl p-tolyl sulfoxide can be used as a nucleophilic reagent to synthesize: Optically active β-disulfoxides by reacting with arenesulfinic esters via formation of α-sulfinylcarbanion. α-substituted N-hydroxylamines by treating with nitrones via preparation of (S)-(-)-methyl p-tolyl sulfoxide anion. 2-O-benzyl-3,4-O-isopropylidene-L-erythrose by one-carbon homologation of 2,3-O-isopropylidene-L-glyceraldehyde.

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

Upstream product

• 52720-03-3 (R)-imino(methyl)(p-tolyl)-λ⁶-sulfanone 
• 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 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 63268-43-9 (+)-(S)-dimethyl-p-tolylsulfinylmethanephosphonate 
• 623-13-2 4-methylphenyl methylsulfide 
• 58044-92-1 S-methyl-S-(4-tolyl)sulfilimine 
• 676-58-4 methylmagnesium chloride 
• 917-64-6 methyl magnesium iodide 
• 443640-88-8 (S_S,S_S)-2-phenyl-1,1-di-p-tolylsulfinyl-ethylene 
• 75-16-1 methylmagnesium bromide 
• 917-54-4 methyllithium 
• 443640-86-6 (S_S,S_S)-1,1-di-p-tolylsulfinyl-3-methyl-but-1-ene 

Downstream Products

• 142722-58-5 (S)-(-)-1-fluoro-3-<(4-methylphenyl)sulphinyl>propan-2-one 
• 113002-37-2 5-Methyl-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 121898-05-3 (S)-(-)-1-chloro-1,1-difluoro-3-<(4-methylphenyl)sulphinyl>propan-2-one 
• 133343-42-7 1-Chloro-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propane-2,2-diol 
• 132164-16-0 (2R,S_S)-(-)-1-chloro-1,1-difluoro-3-(p-tolylsulphinyl)propan-2-ol 
• 133343-49-4 (S)-1-Chloro-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propan-2-ol 
• 133343-44-9 1,1-Dichloro-1-fluoro-3-((S)-toluene-4-sulfinyl)-propane-2,2-diol 
• 132164-18-2 (2R,S_S)-1,1-Dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>propan-2-ol 
• 133343-51-8 (S)-1,1-Dichloro-1-fluoro-3-((S)-toluene-4-sulfinyl)-propan-2-ol 
• 133343-43-8 1-Bromo-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propane-2,2-diol 
• 132164-17-1 (R)-1-Bromo-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propan-2-ol 
• 133343-50-7 (S)-1-Bromo-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propan-2-ol 
• 150993-20-7 1,3-Dimethyl-6-[2-((S)-toluene-4-sulfinyl)-acetyl]-1H-pyrimidine-2,4-dione 
• 24702-26-9 S-p-Tolyl-S-methyl-N-p-tosylsulfimid 

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.