169614-59-9

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[2-(4-methoxyphenyl)ethyl]-
• CAS NO: 169614-59-9
• Molecular Formula: C17H15NO3
• Molecular Weight: 281.311
• Mol File: 169614-59-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[2-(4-methoxyphenyl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[2-(4-methoxyphenyl)ethyl]-(169614-59-9)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[2-(4-methoxyphenyl)ethyl]-(169614-59-9)

Safety Data

• Hazardous Substances Data: 169614-59-9(Hazardous Substances Data)

Upstream product

• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 1074-82-4 potassium phtalimide 
• 18217-00-0 1-(2-Chloroethyl)-4-methoxybenzene 
• 637-69-4 4-Methoxystyrene 
• 136918-14-4 phthalimide 
• 52913-16-3 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxyphenyl)-propionic acid 
• 14425-64-0 4-methoxyphenethyl bromide 
• 85-44-9 phthalic anhydride 
• 55-81-2 4-Methoxyphenethylamine 

Downstream Products

• 970-56-9 2-[2-(4-methoxyphenyl)-2-oxo-ethyl]-isoindole-1,3-dione 
• 55-81-2 4-Methoxyphenethylamine 
• 226991-14-6 2-(4-methoxyphenylethyl)-3-<(E)-2-phenylethylidene>-1-isoindolinone 
• 131523-31-4 2-(4-hydroxy-3,5-dimethoxybenzyl)-3-<(E)-2-phenylethylidene>-1-isoindolinone 
• 131523-27-8 2-(4-hydroxyphenylethyl)-3-<(E)-2-phenylethylidene>-1-isoindolinone 

Relevant articles and documents

An Oxidation Study of Phthalimide-Derived Hydroxylactams

A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.

Photoinduced SET phthalimidation of unactivated double bonds and its application to the synthesis of protected phenethylamines

Phthalimide, in equilibrium with its conjugate base, adds photochemically to cyclohexene and aryl-substituted alkenes (photophthalimidation). The efficient, predictable regioselective photophthalimidation of styrenes constitutes a synthetically useful process for the preparation of N-phenethyl-phthalimides. A possible mechanism for the photophthalimidation involves the nucleophilic attack of phthalimide anion on the alkene cation-radical generated by single electron transfer to excited phthalimide.

Photophthalimidation of unactivated double bonds. Synthesis of protected phenethylamines

At low hydroxide ion concentrations, the photoaddition of phthalimide to cyclohexene, indene or styrene derivatives takes place. The cation radical obtained in the electron transfer from the alkene to excited phthalimide is trapped by phthalimide anion. At high hydroxide ion concentrations concerted [2+2] cycloaddition occurs that yields benzazepinediones, whatever the ionization potential of the alkene. The most suitable reaction conditions can be inferred from the observed fluorescence of phthalimide anion.