20871-31-2

Basic information

• Product Name: 1H-Isoindol-1-one, 2,3-dihydro-3-hydroxy-3-(phenylmethyl)-
• CAS NO: 20871-31-2
• Molecular Formula: C15H13NO2
• Molecular Weight: 239.274
• Mol File: 20871-31-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-Isoindol-1-one, 2,3-dihydro-3-hydroxy-3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindol-1-one, 2,3-dihydro-3-hydroxy-3-(phenylmethyl)-(20871-31-2)
• EPA Substance Registry System: 1H-Isoindol-1-one, 2,3-dihydro-3-hydroxy-3-(phenylmethyl)-(20871-31-2)

Safety Data

• Hazardous Substances Data: 20871-31-2(Hazardous Substances Data)

Upstream product

• 136918-14-4 phthalimide 
• 108-88-3 toluene 
• 1589-82-8 phenylmagnesium bromide 
• 13005-36-2 potassium phenylacetate 
• 100-39-0 benzyl bromide 
• 770-09-2 benzyltrimethylsilane 

Downstream Products

• 39142-91-1 3-benzyl-2,3-dihydro-1H-isoindolin-1-one 
• 764669-06-9 (R)-3-benzylisoindolin-1-one 
• 40523-32-8 3-(phenylmethylene)isoindol-1-one 
• 33608-93-4 (E)-2,3-dihydro-3-phenylmethylene-1H-isoindol-1-one 
• 104563-06-6 3-Benzyl-3-(4-hydroxy-phenyl)-2,3-dihydro-isoindol-1-one 

Relevant articles and documents

Erratum: Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor (Aust. J. Chem. (2020) 73(12):1149-1157)

The authors wish to advise of errors in the above paper. In Table 3, footnote C should read 'Crude product contains 4-methylanisole or p-tolyl acetate.' In the left column of text on the same page as Table 3, the second last sentence should read 'When the para-substituted arylacetates 9b and 9c were employed, 4-methylanisole and p-tolyl acetate were detected by 1H NMR analysis of the crude reaction mixtures but no attempts were made to isolate these simple decarboxylation products.'

Photodecarboxylative benzylations of phthalimide in pH 7 buffer: A simple access to 3-arylmethyleneisoindolin-1-ones

Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3- arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization.

SET photochemistry of phthalimide anion and its reactivity with hydrogen donors

The investigation of the photochemistry of phthalimide anion has uncovered its exceptional reactivity with hydrogen donors such as alcohols, toluene, ethers and amines. Photoreactions can be conducted to high conversions and photoadducts are formed in high yield and with predictable regioselectivity. Exploratory studies have revealed that SET from the excited phthalimide anion to phthalimide is a thermodinamically favourable step that produces the electrophilic phthalimidyl radical and is the key step of the process.