19477-73-7

Basic information

• Product Name: 6-BROMO-3 H-ISOBENZOFURAN-1-ONE
• Synonyms: 6-BROMO-3 H-ISOBENZOFURAN-1-ONE;6-bromo-2-benzofuran-1(3H)-one;6-Bromophthalide;6-broMo-1,3-dihydro-2-benzofuran-1-one;1(3H)-Isobenzofuranone, 6-broMo-
• CAS NO: 19477-73-7
• Molecular Formula: C₈H₅BrO₂
• Molecular Weight: 213.03
• Mol File: 19477-73-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 99.5 °C
• Boiling Point: 362.44 °C at 760 mmHg
• Flash Point: 172.998 °C
• Appearance: /
• Density: 1.743g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 6-BROMO-3 H-ISOBENZOFURAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-3 H-ISOBENZOFURAN-1-ONE(19477-73-7)
• EPA Substance Registry System: 6-BROMO-3 H-ISOBENZOFURAN-1-ONE(19477-73-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• Hazardous Substances Data: 19477-73-7(Hazardous Substances Data)

Usage

Chemical Properties

Light red crystal

InChI:InChI=1/C8H5BrO2/c9-6-2-1-5-4-11-8(10)7(5)3-6/h1-3H,4H2

Upstream product

• 86-90-8 4-bromophthalic anhydride 
• 171011-37-3 4-bromo-2-(hydroxymethyl)benzyl alcohol 
• 79669-49-1 5-bromo-2-methylbenzoic acid 
• 87-41-2 2-benzofuran-1(3H)-one 
• 585-76-2 m-bromobenzoic acid 
• 74-95-3 1,1-dibromomethane 
• 50-00-0 formaldehyd 
• 153435-81-5 (3-bromophenyl)(morpholino)methanone 
• 220513-49-5 5-bromo-1,3-dihydroisobenzofuran 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 610-93-5 6-nitrophthalide 
• 57319-65-0 6-aminophthalide 

Downstream Products

• 627909-55-1 5-bromo-2-hydroxymethyl-benzoic acid 
• 1000692-94-3 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(3-oxo-1,3-dihydroisobenzofuran-5-yl)phenyl)cyclopropanecarboxamide 
• 1000692-95-4 5'-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-4-(hydroxymethyl)-2'-methylbiphenyl-3-carboxylic acid 
• 1240500-28-0 5-bromo-2-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid 
• 1240500-32-6 N-(4-methylphenyl)-7-bromo-1-oxo-1H-isothiochromene-3-carboxamide 
• 1016163-89-5 methyl 5-bromo-2- formylbenzoate 
• 1387557-75-6 (R)-3-allyl-6-phenylisobenzofuran-1(3H)-one 
• 100655-92-3 6-bromo-1,3-dihydroisobenzofuran-1-ol 
• 1286176-82-6 2-(benzenesulphonylmethyl)-5-ethylbenzoic acid 
• 1286178-48-0 2-(phenylthiomethyl)-5-ethylbenzoic acid 
• 874569-19-4 6-[4-({[(2-methoxyphenyl)sulfonyl]amino}methyl)phenyl]-3-hydroisobenzofuran-1-one 
• 72985-23-0 6-methylisobenzofuran-1(3H)-one 
• 862081-37-6 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one 
• 862081-38-7 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one 

Relevant articles and documents

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.

Squaramide-catalyzed asymmetric intramolecular oxa-michael reaction of α,β-unsaturated carbonyls containing benzyl alcohol: Construction of chiral 1-substituted phthalans

Organocatalytic enantioselective intramolecular oxa-Michael reactions of benzyl alcohol bearing α,β-unsaturated carbonyls as Michael acceptors are presented herein. Using cinchona squaramide-based organocatalyst, enones as well as α,βunsaturated esters containing benzyl alcohol provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone could be obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.

Synthesis of 3-Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)-Catalyzed C–H Activation

A straightforward and convenient route has been developed for the synthesis of 3-unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)-catalyzed C–H activation. The reaction proceeds through tandem ortho-hydroxymethylation of aryl amide and subsequent intramolecular lactonization.