16824-02-5

Basic information

• Product Name: 3-Ethoxy-1(3H)-isobenzofuranone
• Synonyms: 3-Ethoxy-1(3H)-isobenzofuranone;3-Ethoxyisobenzofuran-1(3H)-one;3-ETHOXYPHTHALIDE
• CAS NO: 16824-02-5
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• Mol File: 16824-02-5.mol

Chemical Properties

• Melting Point: 64-65 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 306.8°C at 760 mmHg
• Flash Point: 125.1°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.000755mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: 3-Ethoxy-1(3H)-isobenzofuranone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethoxy-1(3H)-isobenzofuranone(16824-02-5)
• EPA Substance Registry System: 3-Ethoxy-1(3H)-isobenzofuranone(16824-02-5)

Safety Data

• Hazardous Substances Data: 16824-02-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10O3/c1-2-12-10-8-6-4-3-5-7(8)9(11)13-10/h3-6,10H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 56973-63-8 C₈H₄O₂ 
• 201230-82-2 carbon monoxide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 6940-49-4 3-Bromophthalide 
• 485-47-2 indan-1,2,3-trione hydrate 
• 7664-93-9 sulfuric acid 
• 119-67-5 o-carboxybenzaldehyde 
• 34046-43-0 ethyl 2-formylbenzoate 
• 5720-05-8 4-methylphenylboronic acid 
• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 4122-56-9 methyl o-formylbenzoate 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 557-20-0 diethylzinc 

Downstream Products

• 21615-75-8 3-(4-tolyl)-isobenzofuranone 
• 119-65-3 isoquinoline 
• 491-30-5 1-hydroxyisoquinoline 
• 77632-08-7 2-(benzoyloxyisoquinol-1-ylmethyl)benzoate 
• 24223-06-1 1-(3-oxo-1,3-dihydroisobenzofuran-1-yl)isoquinoline 
• 5467-92-5 isoquinolin-1-yl(diphenyl)methanol 
• 119-39-1 phthalazone 
• 33125-69-8 (±)-3-(phenylamino)isobenzofuran-1(3H)-one 

Relevant articles and documents

A Facile Synthesis of 3-Substituted Phthalides

1(3H)-Isobenzofuranone (phthalides) and its derivatives possess a wide range of biological activities. A new method was found for the synthesis of 3-substituted phthalides featured with the convenient condensation reaction of 3-ethoxyphthalide with carbanions in high yields.

Synthesis of Enantioenriched Phthalide and Isoindolinone Derivatives from 2-Formylbenzoic Acid

Transformations of 2-formylbenzoic acid provide direct access to a series of heterocyclic organic compounds such as phthalides and isoindolinones. Here, we use (+)-cinchonine as a catalyst in conjunction with nonafluoro-tert-butanol as a hydrogen-bond donor to afford enantiomerically enriched acylated 3-hydroxyphthalides with up to 99% yield and 90% ee through dynamic kinetic resolution. Moreover, various 3-alkoxyphthalides as well as 2-alkyl-3-hydroxy-1-isoindolinones were synthesized from 2-formylbenzoic acid.

Oxidative cyclization of dialdehydes with alcohols and 1,3-dicarbonyl compounds under Rh(III)/Cu(II) conditions

For the preparation of 3-alkoxyphthalides from phthalaldehydes and alcohols, a cyclization reaction in the presence of a rhodium(III) catalyst and copper(II) salt is reported. Cyclization of phthalaldehydes also occurs with 1,3-dicarbonyl compounds under similar conditions to produce 3-substituted phthalides in good yields. An acylrhodium(III) species might be a key intermediate in these cyclization reactions.

Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: Efficient access to chiral 3-substituted phthalides

Transition metal-catalyzed addition of arylboronic acids to 2-formylbenzoates afforded 3-substituted phthalides. By using SPINOL-based phosphites as ligands, a Rh(i)-catalyzed asymmetric version of such an addition reaction was achieved. The Royal Society of Chemistry 2010.

Assignment of the absolute configuration of concentricolide - absolute configuration determination of its bioactive analogs using DFT methods

The configuration of concentricolide was assigned as (S). The configuration of its three analogs, which have anti-HIV-1 activity, were predicted by optical rotation values obtained by the B3LYP/aug-cc-pVDZ//B3LYP/6-31+G(d) and B3LYP/ aug-cc-pVDZ//MP2/6-31

New efficient route to fused aryltetrahydroindolizinones via N-Acyliminium intermediates

Straightforward routes to fused tetrahydroindolizinones by two routes A and B, starting either from. 2-formylbenzoic acid and esters or from, β-hydroxy lactones via acyl iminium ions, are described. A plausible mechanism and limitations are given. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Synthesis of alkyl 2,5-dihydro-5-oxofuran-2-carboxylates via palladium-catalyzed carbonylative cyclization of β-bromovinyl aldehydes in alcohols

β-Bromovinyl aldehydes reacts with carbon monoxide and alcohols at 125 °C in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding carbonylative cyclized alkyl 2,5-dihydro-5-oxofuran-2-carboxylates in good yields. A reaction pathway involving intramolecular addition of acylpalladium to formyl group is proposed as a key step of this catalytic process.

Solid-phase synthesis of isoindolinones and naturally-occurring benzobutyrolactones (phthalides) using a cyclative-cleavage approach

Starting from Merrifield resin, 2-formylbenzoic acids were immobilized on solid supports. Reactions between immobilized 2-formylbenzoic acids and different organometallic reagents (Grignard reagents, zinc reagents, allyl silanes via Sakurai type reactions) furnished secondary alcohols which cyclized depending on the metal counter ion and reaction conditions, forming benzoannelated lactones. Asymmetric synthesis was possible on the resin using chiral [2.2]paracyclophane ligands. While the reaction of immobilized ortho-carboxy benzaldehydes with primary amines at elevated temperatures yielded 3-hydroxyisoindolinones, a reaction at ambient temperature allowed imine formation, which underwent 1,2-addition-cleavage reaction with various nucleophiles, yielding isoindolinones with three points of diversity.

A practical palladium-catalysed heteroannulation of 2-bromobenzaldehyde with alcohols and carbon monoxide leading to 3-alkoxy-3H-isobenzofuran-1-ones

2-Bromobenzaldehyde is carbonylatively cyclised with alcohols in the presence of a catalytic amount of PdCl2(PPh3)2/PPh3 together with a base to afford the corresponding 3-alkoxy-3H-isobenzofuran-1-ones in good

Photochemical behavior of indane-1,2,3-trione in degassed alcoholic solutions: Formation of 3-substituted phthalides

Irradiation of indane-1,2,3-trione in degassed alcoholic solutions affords 3-alkoxycarbonylphthalides as the major product together with 3-alkoxyphthalides. 3-Alkoxycarbonylphthalides may be derived from the reaction between alcohols and the spirooxiranone intermediate, generated photochemically by cleavage of the bond between two carbonyl groups of indane-1,2,3-trione via a cyclobutenone biradical derivative.