87963-59-5

Basic information

• Product Name: 2H-1-Benzopyran-6-carboxaldehyde, 3,4-dihydro-5-hydroxy-2,2-dimethyl-3-(phenylthio)-
• CAS NO: 87963-59-5
• Molecular Formula: C18H18O3S
• Molecular Weight: 314.405
• Mol File: 87963-59-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-6-carboxaldehyde, 3,4-dihydro-5-hydroxy-2,2-dimethyl-3-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-6-carboxaldehyde, 3,4-dihydro-5-hydroxy-2,2-dimethyl-3-(phenylthio)-(87963-59-5)
• EPA Substance Registry System: 2H-1-Benzopyran-6-carboxaldehyde, 3,4-dihydro-5-hydroxy-2,2-dimethyl-3-(phenylthio)-(87963-59-5)

Safety Data

• Hazardous Substances Data: 87963-59-5(Hazardous Substances Data)

Upstream product

• 54287-99-9 5-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde 
• 882-33-7 diphenyldisulfane 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 108-98-5 thiophenol 

Downstream Products

• 91078-11-4 5-Methoxymethoxy-2,2-dimethyl-3-phenylsulfanyl-chroman-6-carbaldehyde 
• 91078-12-5 3-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl-)-1-(2-hydroxy-4-methoxymethoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Synthesis of the Phytoalexin (+/-)-Phaseollin: 3-Phenylthiochromans as Masked 2H-Chromenes and o-Prenyl Phenols

Phenylthiyl radicals are shown to add regiospecifically to 2H-chromenes to afford 3-phenylthiochromans (8), (10), (13), (14), and (15).The sulphide (15), as equivalent to a chromene protected against acid and oxidation, has been used in two syntheses of (+/-)-phaseollin, a major phytoalexin of beans and other legumes, via the sequence (17)->(18)->(19)->(20)->(21)->(+/-)-(1) or (19)->(22)->(23)->(+/-)-(1).Also the 3-phenylthiochromans, on electron transfer from metal naphthalenide or a mercury cathode, open to o-prenylphenols, providing a two step route to biogenetically important phenols from chromenes which is tolerant of free phenol and carbonyl functions and trisubstituted double bonds.

A New Synthesis of o-Prenyl Phenols

Phenylthiyl radicals add regiospecifically to isoprenoid chrom-3-enes to yield 3-phenylthiochromans which open to o-prenylphenols on electron transfer from metal naphthalenides or a mercury cathode; the two-step process is tolerant of free phenol and carbonyl functions, and trisubstituted double bonds.