3700-55-8

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-(2-hydroxypropyl)-
• CAS NO: 3700-55-8
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Mol File: 3700-55-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2-hydroxypropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2-hydroxypropyl)-(3700-55-8)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-(2-hydroxypropyl)-(3700-55-8)

Safety Data

• Hazardous Substances Data: 3700-55-8(Hazardous Substances Data)

Usage

Chemical Class

Isoindolinones

Physical State

White solid

Molecular Weight

201.21 g/mol

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Functional Group

Hydroxypropyl group

Potential Applications

Drug formulations, reagent in organic synthesis, materials science, and as a chemical intermediate in the manufacturing of other organic compounds.

Upstream product

• 29588-90-7 (2S,3R)-3-hydroxy-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)butyric acid 
• 67-56-1 methanol 
• 85-44-9 phthalic anhydride 
• 78-96-6 3-amino-2-propanol 

Downstream Products

• 550-44-7 N-methylphthalimide 
• 3416-57-7 N-acetonylphthalimide 
• 136918-14-4 phthalimide 
• 4775-29-5 3-ethyl-3-hydroxy-2-methyl-2,3-dihydroisoindol-1-one 
• 78-96-6 3-amino-2-propanol 
• 1161742-05-7 (+/-)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-methylethyl 4-chloro-3-nitrobenzoate 
• 1161742-04-6 (+/-)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-methylethyl 2,5-difluorobenzoate 
• 1158349-33-7 (+/-)-O-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-methylethyl] 4-chlorophenyl(3-nitrobenzoyl)thiocarbamate 
• 128191-85-5 (+)-1-Phthaloyl-2-(p-toluolsulfonyloxy)propan 
• 4770-23-4 3-benzyl-3-hydroxy-2-methyl-1,3-dihydroisoindol-1(3H)-one 
• 160113-39-3 o-Tolyl-carbamic acid 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-methyl-ethyl ester 

Relevant articles and documents

Chiral photocages based on phthalimide photochemistry

A new class of photoremovable protecting groups, based on a photoinduced decarboxylation reaction coupled with the elimination of the caged molecule, is described for 2-phthalimido-3-hydroxy-propionate derivatives. When derived from enantiopure N-phthaloyl- serine or threonine, the chirality of the starting amino acid is transmitted to the protected (caged) molecule. These photocages possess good properties for their use in biological systems, and the introduction of chirality opens new possibilities for the study of diastereoselective photochemistry and stereodifferentiation processes involving the release of the caged molecule. Copyright

Acid-mediated intramolecular cationic cyclization using an oxygen atom as internal nucleophile: Synthesis of substituted oxazolo-, oxazino- and oxazepinoisoindolinones

Efficient assembly of substituted oxazolo-, oxazino-, and oxazepinoisoindolinones (5-7, 12-15 and 19) is described in three steps according to an acidic α-oxoamidoalkylation reaction from ready available phthalic anhydride by successive imidation, sodium borohydride reduction and intramolecular cationic cyclization involving N-acyliminium species. The relative stereochemistry accompanying these reactions was also discussed.

Photochemistry of N-phthaloyl derivatives of electron-donor-substituted amino acids

The hydroxy substituted amino acids threonine and serine have been investigated concerning their photochemical behaviour when activated as N-phthaloyl substrates. The methyl esters 1a and 2a solely underwent cleavage of the central C-C single bond to give the glycine derivative 3 and an aldehyde fragment. C-unprotected threonine derivative 1b is converted into a series of products the composition of which depends on solvent polarity and on the electronic state. Three reaction modes were detected for the N-phthaloyl derivatives of the aryl substituted amino acids phenylalanine, tyrosine, and dihydroxyphenylalanine (DOPA): (A) decarboxylation (only for 12a), (B) β-fragmentation, and (C) ring enlargement reaction. Processes B and C are initiated by photo electron transfer (PET), as the solvent dependence revealed. The DOPA derivatives 14a and 14b are the most prominent examples due to their exclusive PET reactivity leading to type C products (18a,b) with high diastereoselectivity (90:10). PET results from the first excited singlet states of 12 and 13, whereas for compounds 14 the corresponding triplet states are involved. The correlation between photochemical reactivity and the fluorescence decay data for compounds 12a,b and 15 is discussed.