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

Description

4-Bromo-2-benzofuran-1(3H)-one is an organic compound characterized by the presence of a benzofuran ring with a bromine atom at the 4-position and a ketone group at the 1-position. It serves as a key intermediate in the synthesis of various pharmaceutical compounds and has demonstrated potential in the development of new drugs.

Uses

Used in Pharmaceutical Synthesis:
4-Bromo-2-benzofuran-1(3H)-one is used as a versatile reactant in the preparation of Citalopram (C505000) analogs via Suzuki coupling. This application is significant for the development of new antidepressant medications, as Citalopram is a widely prescribed selective serotonin reuptake inhibitor (SSRI).
Used in Cardiovascular Applications:
In the pharmaceutical industry, 4-Bromo-2-benzofuran-1(3H)-one is used as a precursor in the synthesis of butylphthalide derivatives, which possess vasorelaxant activity. These compounds have potential applications in the treatment of cardiovascular diseases, as they can help to relax blood vessels and improve blood flow.
Used in Antibacterial Drug Development:
4-Bromo-2-benzofuran-1(3H)-one is also utilized in the synthesis of Pentacyclines, which are Tetracycline (T291400) analogs. Tetracyclines are a class of broad-spectrum antibiotics that are effective against a wide range of bacterial infections. The development of new analogs can help to address the growing issue of antibiotic resistance and provide alternative treatment options for various infections.
Overall, 4-Bromo-2-benzofuran-1(3H)-one plays a crucial role in the synthesis of various pharmaceutical compounds, with applications in the development of antidepressants, cardiovascular treatments, and antibacterial drugs. Its versatility as a reactant makes it a valuable component in the ongoing pursuit of new and effective medications.

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

Downstream Products

• 90483-95-7 3-cyano-phthalide 
• 1345881-90-4 4-(2-hydroxy-3,4-dimethoxyphenyl)isobenzofuran-1(3H)-one 
• 1345880-99-0 [2,3-dimethoxy-6-(1-oxo-3H-isobenzofuran-4-yl)phenyl]propanoate 
• 1345713-00-9 4-(3,4-dimethoxy-2-methoxymethoxyphenyl)-3H-isobenzofuran-1-one 
• 1287277-22-8 methyl 3-bromo-2-formylbenzoate 

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.).