24410-59-1

Basic information

• Product Name: 5-FLUOROBENZOFURAN
• Synonyms: 5-FLUOROBENZOFURAN;5-fluoro-1-benzofuran;Benzofuran, 5-fluoro-;5-Fluoro[b]benzofuran
• CAS NO: 24410-59-1
• Molecular Formula: C₈H₅FO
• Molecular Weight: 136.12
• Mol File: 24410-59-1.mol

Chemical Properties

• Boiling Point: 171.699 °C at 760 mmHg
• Flash Point: 57.642 °C
• Appearance: /
• Density: 1.231 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DCM, Ethyl Acetate
• CAS DataBase Reference: 5-FLUOROBENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUOROBENZOFURAN(24410-59-1)
• EPA Substance Registry System: 5-FLUOROBENZOFURAN(24410-59-1)

Safety Data

• Hazardous Substances Data: 24410-59-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-FLUOROBENZOFURAN is used as a pharmaceutical compound for its dual affinity to the 5-HT1A receptor and serotonin transporter. This unique property allows it to potentially modulate serotonin levels in the brain, which can be beneficial in the treatment of various neurological and psychiatric disorders, such as depression, anxiety, and other mood-related conditions.
Used in Research and Development:
In the field of research and development, 5-FLUOROBENZOFURAN can be utilized as a starting material or a key intermediate in the synthesis of more complex molecules with potential therapeutic applications. Its dual affinity for the 5-HT1A receptor and serotonin transporter makes it an attractive candidate for the development of novel drugs targeting these pathways.
Used in Drug Design and Optimization:
5-FLUOROBENZOFURAN can be employed in drug design and optimization processes, where its unique chemical structure and dual affinity properties can be leveraged to create new molecules with improved pharmacological profiles. This can lead to the development of more effective and safer drugs for the treatment of various medical conditions.

InChI:InChI=1S/C8H5FO/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5H

Upstream product

• 59769-37-8 2-(4-Fluorophenoxy)-acetaldehyde Diethyl Acetal 
• 371-41-5 4-Fluorophenol 

Downstream Products

• 245762-35-0 5-fluoro-2,3-dihydrobenzofuran 
• 1381964-92-6 5-fluoro-2-phenylbenzo[b]furan 
• 65540-47-8 5-fluoro-2-(4'-methoxyphenyl)benzo[b]furan 
• 60770-66-3 5-fluoro-2-methylbenzofuran 
• 473416-33-0 (5-fluorobenzofuran-2-yl)boronic acid 
• 245762-37-2 5-fluoro-7-hydroxy-2,3-dihydrobenzofuran 
• 245762-36-1 5-fluoro-2,3-dihydrobenzofuran-7-carbaldehyde 

Relevant articles and documents

Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis

We report an enantio- and diastereoselective, complete hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis. The developed protocol facilitates the controlled installation of up to six new defined stereocenters and produces architecturally complex octahydrobenzofurans, prevalent in many bioactive molecules. A unique match of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor act in sequence to enable the presented process.

Biocatalytic Strategy for Highly Diastereo- and Enantioselective Synthesis of 2,3-Dihydrobenzofuran-Based Tricyclic Scaffolds

2,3-Dihydrobenzofurans are key pharmacophores in many natural and synthetic bioactive molecules. A biocatalytic strategy is reported here for the highly diastereo- and enantioselective construction of stereochemically rich 2,3-dihydrobenzofurans in high enantiopurity (>99.9% de and ee), high yields, and on a preparative scale via benzofuran cyclopropanation with engineered myoglobins. Computational and structure-reactivity studies provide insights into the mechanism of this reaction, enabling the elaboration of a stereochemical model that can rationalize the high stereoselectivity of the biocatalyst. This information was leveraged to implement a highly stereoselective route to a drug molecule and a tricyclic scaffold featuring five stereogenic centers via a single-enzyme transformation. This work expands the biocatalytic toolbox for asymmetric C–C bond transformations and should prove useful for further development of metalloprotein catalysts for abiotic carbene transfer reactions.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Palladium-Catalyzed Dearomatizing Difunctionalization of Indoles and Benzofurans

A palladium-catalyzed dearomatizing difunctionalization of N-Boc-indoles and benzofurans to give tricyclic indolines and 2,3-dihydrobenzofurans with a fully substituted carbon center is described. Product formation occurs under mild conditions at room temperature with commercially available aryl boronic acids and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a mild oxidant in good yields. 2-Carboxyalkyl-substituted indoles and benzofurans react under Pd-catalysis with aryl boronic acids and TEMPO through dearomatizing arylation/cyclization to the corresponding indolines and dihydrobenzofurans containing a lactone moiety bearing a fully substituted carbon center.

Visible light-induced monofluoromethylenation of heteroarenes with ethyl bromofluoroacetate

Visible light-induced monofluoromethylenation of benzofurans and benzothiophenes with ethyl bromofluoroacetate was developed. This method provided a convenient access to novel α-fluoro-α-heteroarylesters under mild reaction conditions.

Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals

An efficient and environmentally benign heterogeneous catalytic process for the synthesis of 2,3-unsubstituted benzo[b]furans has been established via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals. By utilizing tin-exchanged H-β zeolite (Sn-β) as catalyst, a wide range of functionalized 2,3-unsubstituted benzo[b]furans could be prepared in good to excellent yields. The Sn-β zeolite catalyst also exhibited excellent shape selectivity on the cyclization of meta-substituted 2-aryloxyacetaldehyde acetals, and 6-substituted isomers were preferably formed up to 97% regio-selectivity. Moreover, Sn-β zeolite could be easily recovered and reused without any noticeable activity loss.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

PREPARATION OF BENZOFURANS AND USE THEREOF AS SYNTHETIC INTERMEDIATES

The present invention provides several synthetic methods for preparing N-(2-butylbenzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide, a compound of formula (3), an intermediate in the preparation of Dronedarone. The present invention further provides a process for preparing Dronedarone, comprising the steps of converting 2-butyl-5-bis(methanesulfon)-amidobenzofuran of formula (3) to Dronedarone, wherein the 2-butyl-5-bis(methanesulfon)-amidobenzofuran of formula (3) is prepared by the processes of the present invention.