114129-50-9

Basic information

• Product Name: Naphthalene, 2-(methylsulfinyl)-, (S)-
• Synonyms: .(R)-2-naphthyl methyl sulfoxide;(R)-(+)-methyl 2-naphthyl sulfoxide;.(R)-methyl 2-naphthylsulfoxide;.(R)-2-methanesulfinylnaphthalene;.(R)-methyl 2-naphthyl sulfoxide;.2-naphthyl methyl sulfoxide
• CAS NO: 114129-50-9
• Molecular Formula: C11H10OS
• Molecular Weight: 190.26100
• Mol File: 114129-50-9.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 384.2±11.0 °C(Predicted)
• Density: 1.25±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Naphthalene, 2-(methylsulfinyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 2-(methylsulfinyl)-, (S)-(114129-50-9)
• EPA Substance Registry System: Naphthalene, 2-(methylsulfinyl)-, (S)-(114129-50-9)

Safety Data

• Hazardous Substances Data: 114129-50-9(Hazardous Substances Data)

Upstream product

• 7433-79-6 2-methylthionaphthalene 
• 1308834-02-7 2-(2-naphthylsulfanyl)ethyl phenyl sulfone 
• 1308833-67-1 2-(naphthylsulfinyl)ethyl phenyl sulfone 
• 74-88-4 methyl iodide 
• 91-60-1 2-Naphthalenethiol 
• 35330-76-8 2-methanesulfinylnaphthalene 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 35330-76-8 2-methanesulfinylnaphthalene 

Relevant articles and documents

Titanium-Catalyzed, Asymmetric Sulfoxidation of Alkyl Aryl Sulfides with Optically Active Hydroperoxides

The Ti-catalyzed, asymmetric oxidation of alkyl aryl sulfides by enantiomerically pure hydroperoxides (ee >99%) has been examined. Enantioselectivities with ee values up to ca. 80% were achieved for the oxygen transfer from (S)-(-)-1-phenylethyl hydroperoxide 2a to methyl phenyl and methyl p-tolyl sulfide 1a in CCl4 as solvent, but with much overoxidation to the corresponding sulfone 4. Detailed mechanistic studies showed that the enantioselectivity of the sulfide 1a oxidation results from a combination of a rather low (ee values >20%) asymmetric induction in the sulfoxidation and an effective kinetic resolution (ee values ca. 80% at 85% sulfide conversion) of the sulfoxide 3a by enantioselective oxidation to the sulfone 4a. The overoxidation (loss of chemoselectivity) is due to sulfoxide coordination to the Ti metal to generate a template in which the oxygen atom is intramolecularly transferred from the bound and activated, optically active hydroperoxide to the ligated sulfoxide in a stereocontrolled manner.

Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations

Here we report a methionine sulfoxide reductase A (MsrA) homologue with extremely high substrate tolerance and a wide substrate scope for the biocatalytic preparation of enantiopure sulfoxides. This MsrA homologue which was obtained from Pseudomonas alcaliphila (named paMsrA) showed good activity and enantioselectivity towards a series of aryl methyl/ethyl sulfoxides 1a-1k, with electron-withdrawing or electron-donating substituents at the aromatic ring. Chiral sulfoxides in the R configuration were prepared with approximately 50% of yield and up to 99% enantiomeric excess through the asymmetric reductive resolution of racemic sulfoxide catalyzed by the recombinant paMsrA protein. More importantly, kinetic resolution has been successfully accomplished with high enantioselectivity (E > 200) at initial substrate concentrations up to 320 mM (approximately 45 g L-1), which represents a great improvement in the aspect of the substrate concentration for the biocatalytic preparation of chiral sulfoxides.

Efficient HPLC enantiomer separation using a pillared homochiral metal-organic framework as a novel chiral stationary phase

HPLC enantioseparation of racemates using novel pillared homochiral metal-organic framework-silica composite as chiral stationary phase has been successfully demonstrated.