102308-43-0

Basic information

• Product Name: 4-BROMO-2-BENZOFURAN-1(3H)-ONE
• Synonyms: 4-BROMOPHTHALIDE;4-BROMO-3H-ISOBENZOFURAN-1-ONE;4-BROMO-2-BENZOFURAN-1(3H)-ONE;4-broMo-1,3-dihydro-2-benzofuran-1-one;4-BROMOISOBENZOFURAN-1(3H)-ONE;4-Bromo-3H-isobenzofuran-1-one, 4-Bromobenzo[c]furan-1(3H)-one;4-Bromo-1(3H)-isobenzofuranone
• CAS NO: 102308-43-0
• Molecular Formula: C₈H₅BrO₂
• Molecular Weight: 213.03
• EINECS: 200-589-5
• Mol File: 102308-43-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 103-104 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 378.209 °C at 760 mmHg
• Flash Point: 182.534 °C
• Appearance: /
• Density: 1.743 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BROMO-2-BENZOFURAN-1(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-BENZOFURAN-1(3H)-ONE(102308-43-0)
• EPA Substance Registry System: 4-BROMO-2-BENZOFURAN-1(3H)-ONE(102308-43-0)

Safety Data

• Hazardous Substances Data: 102308-43-0(Hazardous Substances Data)

Usage

Uses

4-Bromo-2-benzofuran-1[3H]-one is a versatile reactant used in various syntheses. It is used in preparation of Citalopram (C505000) analogs via Suzuki coupling. 4-Bromo-2-benzofuran-1[3H]-one is used in the synthesis of butylphthalide derivatives possessing vasorelaxant activity. Also used in the synthesis of Pentacyclines that are Tetracycline (T291400) analogs.

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

Upstream product

• 59434-19-4 4-Amino-1(3H)-isobenzofuranon 
• 82-73-5 3-bromophthalic anhydride 
• 76006-33-2 3-bromo-2-methylbenzoic acid 
• 50-00-0 formaldehyd 
• 153435-81-5 (3-bromophenyl)(morpholino)methanone 
• 99548-54-6 methyl 3-bromo-2-methylbenzoate 
• 103260-67-9 4-acetylamino-phthalide 
• 65399-18-0 4-nitrophthalide 
• 6296-53-3 3-acetylaminophthalic anhydride 
• 87-41-2 2-benzofuran-1(3H)-one 
• 116-69-8 3-bromophthalic acid 
• 576-23-8 2,3-dimethylbromobenzene 
• 526-75-0 2,3-Dimethylphenol 

Downstream Products

• 90483-95-7 3-cyano-phthalide 
• 1287277-22-8 methyl 3-bromo-2-formylbenzoate 
• 1345713-00-9 4-(3,4-dimethoxy-2-methoxymethoxyphenyl)-3H-isobenzofuran-1-one 
• 1345880-99-0 [2,3-dimethoxy-6-(1-oxo-3H-isobenzofuran-4-yl)phenyl]propanoate 

Relevant articles and documents

Ligand-enabled pd(ii)-catalyzed c(sp3)-h lactonization using molecular oxygen as oxidant

Pd(II)-catalyzed C-H lactonization of o-methyl benzoic acid substrates has been achieved using molecular oxygen as the oxidant. This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis as well as a method to construct biologically important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing.

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On the regioselectivity of metal hydride reductions of 3-substituted phthalic anhydrides

A problem of 3-methoxyphthalide reduction by metal hydrides was reinvestigated. Various effects controlling selectivity of reductions in 3-substituted phthalides were studied, and a qualitative interpretation of the results is now proposed. Methods for obtaining enhanced yields of one or the other lactonic product were developed.

Palladium (II)-Catalyzed Decarboxylative Cross-Dehydrogenative Coupling: Direct Synthesis of meta-Substituted Biaryls from Aromatic Acids

A palladium-catalyzed tandem process of simple aromatic acids has been achieved to afford meta-substituted biaryls in moderate to good yields. The reaction proceeds via carboxyl-directed intermolecular cross-dehydrogenative coupling and subsequent decarboxylation. The new C?C bonds in this transformation are formed in the ortho position of carboxyl and the reaction tolerates electron-rich acids. Both symmetrical and unsymmetrical meta-substituted biaryls can be directly synthesized via this method. (Figure presented.).