26486-93-1

Basic information

• Product Name: 2,3-dihydro-3-hydroxy-1H-isoindol-1-one
• Synonyms: 2,3-dihydro-3-hydroxy-1H-isoindol-1-one;3-Hydroxy-2H-isoindole-1(3H)-one;3-Hydroxyisoindolin-1-one;3-HYDROXYPHTHALIMIDINE
• CAS NO: 26486-93-1
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.14668
• EINECS: 247-732-9
• Mol File: 26486-93-1.mol

Chemical Properties

• Boiling Point: 439.4°C at 760 mmHg
• Flash Point: 219.5°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 1.7E-08mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: 2,3-dihydro-3-hydroxy-1H-isoindol-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydro-3-hydroxy-1H-isoindol-1-one(26486-93-1)
• EPA Substance Registry System: 2,3-dihydro-3-hydroxy-1H-isoindol-1-one(26486-93-1)

Safety Data

• Hazardous Substances Data: 26486-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2,3-dihydro-3-hydroxy-1H-isoindol-1-one is utilized as a key intermediate in the production of various pharmaceuticals and agrochemicals. Its unique structure and functional groups make it a valuable component in the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Organic Synthesis and Material Science:
In the realm of organic synthesis, 2,3-dihydro-3-hydroxy-1H-isoindol-1-one serves as a versatile building block for the creation of complex organic molecules. Its presence in material science is attributed to its potential to form novel materials with unique properties, such as improved stability or specific interactions with other molecules.
Used in Medicinal Chemistry for Antimicrobial and Antifungal Applications:
2,3-dihydro-3-hydroxy-1H-isoindol-1-one is employed as an antimicrobial and antifungal agent due to its moderate to strong activity against various microorganisms. This makes it a candidate for further research and development in the field of medicinal chemistry, with potential applications in the treatment of infections and the development of new antimicrobial agents.

InChI:InChI=1/C8H7NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4,7,10H,(H,9,11)

Upstream product

• 26487-02-5 3-ethoxy-2,3-dihydro-1H-isoindol-1-one 
• 67-56-1 methanol 
• 33081-78-6 sodium phthalimide 
• 87093-74-1 (acetyl-5 6H-thiazine-1,3 yl-2)-2 phtalimido-2 propionate de methyle 
• 69775-41-3 1-Benzamido-2-benzoxypropane 
• 68-12-2 N,N-dimethyl-formamide 
• 110-83-8 cyclohexene 
• 136918-14-4 phthalimide 
• 123-91-1 1,4-dioxane 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 6940-49-4 3-Bromophthalide 
• 7664-41-7 ammonia 
• 71-43-2 benzene 

Downstream Products

• 26487-02-5 3-ethoxy-2,3-dihydro-1H-isoindol-1-one 
• 93679-80-2 3-p-toluidino-isoindolin-1-one 
• 109499-96-9 benzoic acid-[N'-(3-oxo-isoindolin-1-yl)-hydrazide] 
• 93679-79-9 3-phenethylamino-isoindolin-1-one 
• 6266-49-5 2-phenylphthalazin-1-one 
• 87-41-2 2-benzofuran-1(3H)-one 
• 88-97-1 phthalamic acid 
• 119-39-1 phthalazone 
• 51484-19-6 3-benzyl-3,4-dihydro-2H,10bH-[1,3,5]oxadidiazanediylidene[2,3-a]isoindol-6-one 
• 1272664-39-7 (R)-3-(6-benzyloxy-1H-indol-3-yl)isoindolin-1-one 
• 1272664-38-6 (R)-3-(5-benzyloxy-1H-indol-3-yl)isoindolin-1-one 
• 1272664-37-5 (R)-3-(4-benzyloxy-1H-indol-3-yl)isoindolin-1-one 
• 1373426-82-4 (E)-3-(2-phenylethenyl)isoindolin-1-one 

Relevant articles and documents

Synthesis of Isoindoles. Acid or Base Induced Cyclization of 2-Cyanobenzaldehyde with Alcohols

Various 3,3-dialkoxy-2,3-dihydro-1-hydroxy-1H-isoindoles (2) were obtained by treating 2-cyanobenzaldehyde (1) with alcohols in the presence of an acid catalyst such as silica gel.In the reaction using a base catalyst such as triethylamine and 1,8-diazabi

One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles

A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.

FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted benzimidazole, imidazo[1,2-α]pyridine and pyrazolo[1,5- α]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human a

Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.

A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins

A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF 3·OEt2 at room temperature. For most of the olefins,the reactions afforded the Csp3-Csp2 cross-coupling products,but for the α-methylstyrene and 1-hexene,the Csp3-Csp3 cross-coupling products were obtained.

Unexpected course of rearrangement of substituted S-(1(3H)- isobenzofuranone-3-yl)isothiuronium bromides

Three series of S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides differing in substitution at the isothiuronium moiety (none, one or two methyl groups) and at the benzene ring were prepared and characterized. These salts were then treated with variou

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.

The investigation of nucleophilic reactions of 3 -bromo/chloro phthalide with amines

The reaction of 3-bromo/chloro phthalide 1a/b with secondary amines in polar solvents gives the corresponding amides of 2-formylbenzoic acid, while in nonpolar solvents gives 3-aminophthalides. The reaction of 1a/b with aromatic primary amines gives 3-arylaminophthalides, while with aliphatic primary amines 3-hydroxyphthalimidines are obtained.

Low-valent titanium induced reduction of phthalimides and coupling of corresponding isoindoles

A new method for the reduction of N-substituted phthalimides to the corresponding hydroxy lactams and the coupling of hydroxy lactams is described. We performed the reactions, which induced by low-valent titanium reagent in the aromatic solvent and in the

Reactions of carbonyl compounds in basic solutions. Part 28. The alkaline hydrolysis of 2-formylbenzonitrile, N-(2-formyl and -acetylphenyl)acetamides, N-(2-formylphenyl)-substituted benzamides, 4-(2-formylbenzoyl)morpholine, 3-(4-morpholino)- and -(N-methylanilino)-phthalides and -na

Rate coefficients have been measured for the alkaline hydrolysis of 2-formylbenzonitrile 1, N-(2-formyl and -acetylphenyl)acetamides 2, N-(2-formylphenyl)-3-substituted benzamides 3, 4-(2-formylbenzoyl)morpholine 4, 3-(4-morpholino)- and -(N-methylanilino)-phthalides 5 and -naphthalides 6 in 70percent (v/v) dioxane-water at various temperatures.The enthalpies and entropies of activation have been evaluated.The hydrolysis of the nitrile is second order in base and that of the amides is first order in base.The relative rates of hydrolysis, activation parameters and substituent effects have been used to suggest the mechanisms of the reactions.Intramolecular catalysis by the neighbouring carbonyl group occurs in the alkaline hydrolysis of 1-4.The alkaline hydrolysis of 5 and 6 is rapid due to their lactone structures.