4732-72-3

Basic information

• Product Name: Benzofuran-2,3-dione
• Synonyms: 2,3-Benzofurandione;2,3-Dihydrobenzofuran-2,3-dione;Benzofuran-2,3-dione;Oxisatin;NSC 122748;3-oxobenzofuran-2-one
• CAS NO: 4732-72-3
• Molecular Formula: C₈H₄O₃
• Molecular Weight: 148.12
• Mol File: 4732-72-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 120℃
• Boiling Point: 228.68°C (rough estimate)
• Flash Point: 132.9°C
• Appearance: /
• Density: 1.444
• Vapor Pressure: 0.00434mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Benzofuran-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: Benzofuran-2,3-dione(4732-72-3)
• EPA Substance Registry System: Benzofuran-2,3-dione(4732-72-3)

Safety Data

• Hazardous Substances Data: 4732-72-3(Hazardous Substances Data)

Usage

General Description

Benzofuran-2,3-dione, also known as dibenzofuran-1,4-dione, is a chemical compound with the molecular formula C8H4O3. It is a yellow solid that is insoluble in water and is primarily used as an intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds. Benzofuran-2,3-dione is a versatile building block in organic chemistry and is often used in the production of heterocyclic compounds, which have applications in drug development and materials science. It is also known to have potential anti-inflammatory and anticancer properties, making it an important compound in pharmaceutical research. However, benzofuran-2,3-dione is considered to be a hazardous chemical and should be handled with caution due to its toxicity and potential health risks.

InChI:InChI=1/C8H4O3/c9-7-5-3-1-2-4-6(5)11-8(7)10/h1-4H

Synthetic route

benzofuran-2,3-dione 2-oxime → coumarandione (4732-72-3)

Conditions	Yield
With hydrogenchloride; acetic acid In water Heating;	87%

spiro[benzofuran-2(3H),2'-[1,3]dithian]-3-one → coumarandione (4732-72-3)

Conditions	Yield
With N-chloro-succinimide; silver nitrate In acetonitrile at 0℃; for 0.0833333h;	50%

indole-2,3-dione (91-56-5) → coumarandione (4732-72-3)

Conditions	Yield
Stage #1: indole-2,3-dione With sodium hydroxide; sodium nitrite In water Cooling with ice; Stage #2: With sulfuric acid In water at 60℃; Cooling with ice;	46%
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 20 °C 1.2: 2.25 h / 0 - 60 °C 2.1: phosphorus pentoxide / toluene / 6 h / Reflux; Dean-Stark View Scheme

(2-hydroxyphenyl)oxoacetic acid (17392-16-4) → coumarandione (4732-72-3)

Conditions	Yield
With acetic anhydride for 0.0833333h; Heating;	29%
bei der Destillation unter vermindertem Druck;
With phosphorus pentaoxide; Petroleum ether
With acetic anhydride Heating;
With phosphorus pentoxide In toluene for 6h; Reflux; Dean-Stark;

2,2'-bi-benzofuranylidene-3,3'-dione (22856-49-1) → coumarandione (4732-72-3)

Conditions	Yield
With chromic acid

o-hydroxyacetophenone (118-93-4) → coumarandione (4732-72-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: SeO2 2: Ac2O / Heating View Scheme

2-trifluoromethylsulfonyloxybenzoic acid ethyl ester (179538-97-7) → coumarandione (4732-72-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.67 h / -40 - -20 °C / Inert atmosphere 1.2: -78 - 25 °C / Inert atmosphere 2.1: N-chloro-succinimide; silver nitrate / acetonitrile / 0.08 h / 0 °C View Scheme

2-hydroxy-benzoic acid ethyl ester (118-61-6) → coumarandione (4732-72-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / dichloromethane; mineral oil; hexane / 0 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.67 h / -40 - -20 °C / Inert atmosphere 2.2: -78 - 25 °C / Inert atmosphere 3.1: N-chloro-succinimide; silver nitrate / acetonitrile / 0.08 h / 0 °C View Scheme

3-Formylchromone (17422-74-1) → coumarandione (4732-72-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite; dipotassium peroxodisulfate / acetone / 20 °C / Green chemistry 2: acetic acid; hydrogenchloride / water / Heating View Scheme

coumarandione (4732-72-3) + 1-methoxybuta-1,3-diene (3036-66-6) → C14H14O3

Conditions	Yield
In toluene at 20℃; under 6000600 Torr; for 12h; Hetero Diels-Alder reaction;	90%

coumarandione (4732-72-3) + benzoyldiazomethane triphenylphosphazine (22610-14-6) → 2-benzoylmethylenehydrazono-2,3-dihydro-3-benzofuranone (540535-89-5)

Conditions	Yield
In toluene at 20℃;	87%

coumarandione (4732-72-3) + C25H20BrOP → 2-(5-bromo-2-hydroxybenzylidene)benzofuran-3(2H)-one

Conditions	Yield
Stage #1: C25H20BrOP With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Wittig Olefination; Stage #2: coumarandione In tetrahydrofuran; hexane at 0℃; for 5.5h; Heating;	81%

coumarandione (4732-72-3) → (2-hydroxy-phenyl)-acetic acid hydrazide (22446-43-1)

Conditions	Yield
With hydrazine hydrate for 0.25h; Heating;	80%

coumarandione (4732-72-3) + (1-methyl-2-oxo-3-indolinylidene)triphenylphosphazine (3265-22-3) → C17H11N3O3

Conditions	Yield
In toluene at 20℃;	76%

benzofuran-2(3H)-one (553-86-6) + coumarandione (4732-72-3) → (E)-[3,3']bibenzofuranylidene-2,2'-dione (80360-47-0)

Conditions	Yield
With phosphorus tribromide at 140℃;

coumarandione (4732-72-3) + 2-chloro-1-(2-methoxy-phenyl)-ethanone (53688-19-0) + sodium ethanolate (141-52-6) → 2-(2-methoxy-benzoyl)-benzofuran-3-carboxylic acid ethyl ester (860691-35-6)

Conditions	Yield
With ethanol

coumarandione (4732-72-3) + 2-chloro-1-(naphthalen-1-yl)ethan-1-one (76469-33-5) → 2-[1]naphthoyl-benzofuran-3-carboxylic acid ethyl ester

Conditions	Yield
With ethanol; sodium ethanolate

coumarandione (4732-72-3) + 2-(2-bromoacetyl)benzoic acid methyl ester (7460-55-1) → 2-(2-carboxy-benzoyl)-benzofuran-3-carboxylic acid

Conditions	Yield
With methanol; sodium methylate Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge;

coumarandione (4732-72-3) + 1-(benzofuran-2-yl)-2-bromoethan-1-one (23489-36-3) → 2-(benzofuran-2-carbonyl)-benzofuran-3-carboxylic acid ethyl ester

Conditions	Yield
With ethanol; sodium ethanolate

coumarandione (4732-72-3) + acetic acid (64-19-7) + aniline (62-53-3) → (2-hydroxy-phenyl)-glyoxylic acid anilide (34073-43-3)

coumarandione (4732-72-3) + acetic acid (64-19-7) + aniline (62-53-3) → (2-hydroxy-phenyl)-phenylimino-acetic acid (52529-40-5)

coumarandione (4732-72-3) + ethyl bromoacetate (105-36-2) → 1-benzofuran-2,3-dicarboxylic acid (131-76-0)

Conditions	Yield
With ethanol; sodium ethanolate Erwaermen des Reaktionsgemisches mit Wasser;

coumarandione (4732-72-3) + 2-bromo-1-o-tolylethanone (51012-65-8) → 2-o-toluoyl-benzofuran-3-carboxylic acid ethyl ester

Conditions	Yield
With ethanol; sodium ethanolate

coumarandione (4732-72-3) + 2-bromo-3'-methylacetophenone (51012-64-7) → 2-m-toluoyl-benzofuran-3-carboxylic acid ethyl ester (109614-97-3)

Conditions	Yield
With ethanol; sodium ethanolate

coumarandione (4732-72-3) + chloroacetic acid (79-11-8) → (2-carboxymethoxy-phenyl)-glyoxylic acid (93334-77-1)

Conditions	Yield
With sodium hydroxide

coumarandione (4732-72-3) + sodium ethanolate (141-52-6) + 1,3-Dichloroacetone (534-07-6) → bis-(3-ethoxycarbonyl-benzofuran-2-yl)-ketone

Conditions	Yield
With ethanol

coumarandione (4732-72-3) + ethanol (64-17-5) + aniline (62-53-3) → (2-hydroxy-phenyl)-glyoxylic acid anilide (34073-43-3)

coumarandione (4732-72-3) + ethanol (64-17-5) + aniline (62-53-3) → (2-hydroxy-phenyl)-phenylimino-acetic acid (52529-40-5)

coumarandione (4732-72-3) + aniline (62-53-3) + benzene (71-43-2) → (2-hydroxy-phenyl)-glyoxylic acid anilide (34073-43-3)

Upstream product

• 22856-49-1 2,2'-bi-benzofuranylidene-3,3'-dione 
• 91-56-5 indole-2,3-dione 
• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 17422-74-1 3-Formylchromone 
• 118-93-4 o-hydroxyacetophenone 
• 17392-16-4 (2-hydroxyphenyl)oxoacetic acid 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 179538-97-7 2-trifluoromethylsulfonyloxybenzoic acid ethyl ester 

Downstream Products

• 22446-43-1 (2-hydroxy-phenyl)-acetic acid hydrazide 
• 21083-33-0 6-oxocyclohexa-2,4-dienylideneketene 
• 2370-96-9 benzolactone 
• 115252-80-7 cyclopentadienylideneketene 
• 17392-16-4 (2-hydroxyphenyl)oxoacetic acid 
• 34073-47-7 C₁₅H₁₂N₂O₄S 
• 1163144-03-3 C₈H₄O₅ 
• 4727-22-4 cyclopentadienylidenemethanone 
• 1440545-09-4 C₂₈H₂₂O₆ 
• 1440545-06-1 C₂₃H₁₉ClO₆ 
• 1440545-05-0 C₂₃H₁₉BrO₆ 
• 1440545-04-9 C₂₄H₂₂O₇ 
• 1440545-01-6 C₂₃H₂₀O₆ 
• 1440545-03-8 C₂₄H₁₉NO₆ 

Relevant articles and documents

TBN-triggered, manipulable annulations of: O -hydroxyarylenaminones for divergent syntheses of oximinochromanones and oximinocoumaranones

Divergent synthesis provides an indispensable route to rapid acquisition of structurally diverse chemical scaffolds from identical starting materials. Herein, we describe unprecedented divergent annulations of o-hydroxyarylenaminones promoted by tert-butyl nitrite (TBN) under mild conditions. Two different types of benzo-oxa-heterocycle, including oximinochromanones and oximinocoumaranones, were smoothly assembled with a broad substrate scope and good functional group compatibility.

A Serendipitous Synthesis of Bis-Heterocyclic Spiro 3(2 H)-Furanones

(Z) Enol triflates 6, 11b-d, (E) enol triflate 11e, and phenol triflate 11a, derived from β-keto esters or 2-carboalkoxy phenols, respectively, react with N-Boc 2-lithiopyrrolidine (5a), N-Boc N-methylaminomethyllithium (5b), or 2-lithio-1,3-dithiane (14) to afford 3(2H)-furanones in modest to good yields (38-81%). Product and carbanion reagent studies suggest that the 3(2H)-furanone is formed in a cascade of reactions involving nucleophilic acyl substitution, enolate formation, trifluoromethyl transfer, iminium or sulfenium ion formation, and subsequent ring closure to form the 3(2H)-furanone. The use of 2-lithio-1,3-dithiane affords a cyclic α-keto-S,S,O-orthoester in which the functionality can be selectively manipulated for synthetic applications. (Chemical Equation Presented).

Photolysis of indan-l,2-dione derivatives in oxygen-doped argon matrix at low temperature

Photolysis of indan-l,2,3-trion (la), benzo[ft]furan-2,3-dione (lb), and N-methylisatin (1c) in argon matrix either with or without oxygen at 10 K was investigated by IR spectroscopy in combination with DFT calculations. The results indicate that while 1a and 1b gave the products mixture as a result of α-cleavage, followed by decarbonylation, 1c was rather photostable under similar conditions. However, when the irradiation was carried out in argon matrix doped with 20% oxygen, 1c decomposed much more efficiently than that in argon matrix and cyclic diacyl peroxide presumably formed by trapping of initial diradical originating from α-cleavage by molecular oxygen was detected. Similar irradiation of 1b also gave cyclic diacyl peroxide along with photodecarbonylation products, but irradiation of 1a in oxygen-doped matrix produced not only cyclic diacyl peroxide but also products as a result of oxidation of photodecarbonylation product. The present observation reveals that photolysis of ketones in oxygen-doped matrix at low temperature provides useful information concerning the reactivities of ketones toward α-cleavage.