320589-21-7

Basic information

• Product Name: 1-(p-tolylsulfinyl)-2-naphthaldehyde dimethyl acetal
• Synonyms: 1-(p-tolylsulfinyl)-2-naphthaldehyde dimethyl acetal
• CAS NO: 320589-21-7
• Molecular Weight: 340.443
• Mol File: 320589-21-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(p-tolylsulfinyl)-2-naphthaldehyde dimethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-tolylsulfinyl)-2-naphthaldehyde dimethyl acetal(320589-21-7)
• EPA Substance Registry System: 1-(p-tolylsulfinyl)-2-naphthaldehyde dimethyl acetal(320589-21-7)

Safety Data

• Hazardous Substances Data: 320589-21-7(Hazardous Substances Data)

Upstream product

• 31536-21-7 isopropyl 4-methylbenzenesulfinate 
• 103668-59-3 1-bromo-2-naphthaldehyde dimethyl acetal 

Downstream Products

• 289473-09-2 1-(p-tolylsulfinyl)-2-naphthaldehyde 

Relevant articles and documents

New asymmetric reactions of 2-formyl- and 2-acyl-1-[(2,4,6-triisopropylphenyl)sulfinyl]naphthalenes via diastereomeric rotamers

Nucleophilic reactions with Grignard reagents and the Mukaiyama aldol reactions of the naphthaldehydes having the (2,4,6-triisopropylphenyl)sulfinyl group produced products with high stereoselectivity. In these reactions, the stereochemistry of the major products changes depending on the Lewis acids used. Reduction of the 2-acyl-1-[(2,4,6-triisopropylphenyl)sulfinyl]naphthalenes also proceeds with high stereoselectivity but with a different stereochemistry depending on the reducing agents. We have demonstrated, by the mechanistic consideration based on the X-ray crystal structures as well as the 1H and 13C NMR spectral data, that the extremely high and specific stereoselectivities of these reactions are due to the predominant rotamer around the C(naph)-S axis. Synthesis of enantiomerically pure 2-naphthylmethanol is provided as an example.