596-28-1

Basic information

• Product Name: 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one
• Synonyms: 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one;1(3H)-Isobenzofuranone, 3,3-bis(3,4-dihydroxyphenyl)-;Nsc87874;Phthalide, 3,3-bis(3,4-dihydroxyphenyl)-;Pyrocatecholphthalein;Pyrocatecholphthlein
• CAS NO: 596-28-1
• Molecular Formula: C₂₀H₁₄O₆
• Molecular Weight: 350.32
• Mol File: 596-28-1.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 658.7 °C at 760 mmHg
• Flash Point: 243.2 °C
• Appearance: /
• Density: 1.546 g/cm³
• Vapor Pressure: 5.87E-18mmHg at 25°C
• Refractive Index: 1.745
• CAS DataBase Reference: 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one(596-28-1)
• EPA Substance Registry System: 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one(596-28-1)

Safety Data

• Hazardous Substances Data: 596-28-1(Hazardous Substances Data)

Usage

General Description

3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one, also known as dibenzofuranone, is a chemical compound with antioxidant properties. It is a member of the flavonoid family, which are known for their potential health benefits. 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one has been studied for its potential role in preventing or treating various diseases due to its antioxidant and anti-inflammatory properties. It has also shown to have anticancer properties in some studies. Overall, 3,3-Bis(3,4-dihydroxyphenyl)isobenzofuran-1(3H)-one is a promising compound with potential health benefits, though further research is needed to fully understand its effects and potential applications.

InChI:InChI=1/C20H14O6/c21-15-7-5-11(9-17(15)23)20(12-6-8-16(22)18(24)10-12)14-4-2-1-3-13(14)19(25)26-20/h1-10,21-24H

Synthetic route

phthalic anhydride (85-44-9) + benzene-1,2-diol (120-80-9) → 3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one (596-28-1)

Conditions	Yield
With zinc(II) chloride at 140 - 150℃;

3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one (596-28-1) + 3,5-dibromo-4-hydroxysalicylic acid (3147-46-4) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → eosin y (15086-94-9)

Conditions	Yield
at 170℃;

3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one (596-28-1) + recorcinol (108-46-3) → fluorescein (2321-07-5)

Conditions	Yield
at 210 - 220℃;

3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one (596-28-1) + diethylamine (109-89-7) → 2-(3,4,5,6-Tetrahydroxy-9H-fluoren-9-yl)-benzoic acid (103507-71-7)

Conditions	Yield
at 145 - 150℃;

3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one (596-28-1) + diethylamine (109-89-7) → 2-(3,6-Bis-ethylamino-4,5-dioxo-5,9-dihydro-4H-fluoren-9-yl)-N-ethyl-benzamide (103211-27-4)

Conditions	Yield
at 145 - 150℃;

Upstream product

• 85-44-9 phthalic anhydride 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 103211-27-4 2-(3,6-Bis-ethylamino-4,5-dioxo-5,9-dihydro-4H-fluoren-9-yl)-N-ethyl-benzamide 
• 103507-71-7 2-(3,4,5,6-Tetrahydroxy-9H-fluoren-9-yl)-benzoic acid 
• 2321-07-5 fluorescein 
• 15086-94-9 eosin y