23489-36-3

Basic information

• Product Name: 1-(1-BENZOFURAN-2-YL)-2-BROMOETHAN-1-ONE
• Synonyms: 2-(2-BROMOACETYL)BENZOFURAN;1-(1-BENZOFURAN-2-YL)-2-BROMOETHAN-1-ONE;1-(1-BENZOFURAN-2-YL)-2-BROMOETHANONE;1-BENZOFURAN-2-YL-2-BROMO-ETHANONE;AKOS BBS-00004078;2-(2-Bromoacetyl)benzo[b]furan;1-(1-Benzofuran-2-yl)-2-bromoethan-1-one, GC 90+%;1-(1-Benzofuran-2-yl)-2-bromoethan-1-one ,97%
• CAS NO: 23489-36-3
• Molecular Formula: C₁₀H₇BrO₂
• Molecular Weight: 239.07
• EINECS: 200-258-5
• Product Categories: Furan&Benzofuran
• Mol File: 23489-36-3.mol

Chemical Properties

• Melting Point: 89 °C
• Boiling Point: 306.782 °C at 760 mmHg
• Flash Point: 139.337 °C
• Appearance: white to light yellow crystal powder
• Density: 1.583 g/cm³
• Vapor Pressure: 0.000755mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 1-(1-BENZOFURAN-2-YL)-2-BROMOETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-BENZOFURAN-2-YL)-2-BROMOETHAN-1-ONE(23489-36-3)
• EPA Substance Registry System: 1-(1-BENZOFURAN-2-YL)-2-BROMOETHAN-1-ONE(23489-36-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-22
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 23489-36-3(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1-(1-Benzofuran-2-yl)-2-bromoethan-1-one is used as a reactant for the Eschenmoser coupling reaction, which is a method for forming carbon-carbon bonds in organic chemistry.
2. Used in Pharmaceutical Industry:
1-(1-Benzofuran-2-yl)-2-bromoethan-1-one is used as a key intermediate in the preparation of β-oxo sulfones, which are substrates for stereoselective Michael addition/cross-benzoin cascade reactions. These reactions are crucial in the synthesis of complex organic molecules with potential pharmaceutical applications.
3. Used in Antimicrobial Applications:
In the pharmaceutical industry, 1-(1-Benzofuran-2-yl)-2-bromoethan-1-one is used as a starting material for the preparation of thienylpyrazole-based thiazoles and pyrazolines. These compounds exhibit antimicrobial, antioxidant, anti-inflammatory, and analgesic properties, making them valuable in the development of new drugs.
4. Used in Antimicrobial Research:
1-(1-Benzofuran-2-yl)-2-bromoethan-1-one is utilized in the synthesis of isatin-(benzofuryl-thiazolyl)-hydrazones by cyclocondensation with isatin-thiosemicarbazones under microwave irradiation. These hydrazones have been found to possess antimicrobial properties, which can be beneficial in the development of new antibiotics.
5. Used in DNA Protection Research:
In the field of biochemistry, 1-(1-Benzofuran-2-yl)-2-bromoethan-1-one is used in the synthesis of 2-naphthyl ethers. These compounds serve as protective agents against DNA damage induced by bleomycin-iron, which can be useful in the development of treatments for DNA damage-related diseases.
6. Used in Asymmetric Synthesis:
In the field of catalysis, 1-(1-Benzofuran-2-yl)-2-bromoethan-1-one is employed in the asymmetric synthesis of β-dialkylamino alcohols by Ru-catalyzed transfer hydrogenation of α-dialkylamino ketones. This process is essential for the production of enantiomerically pure compounds, which are crucial in the pharmaceutical industry for the development of chiral drugs with improved efficacy and reduced side effects.

InChI:InChI=1/C10H7BrO2/c11-6-8(12)10-5-7-3-1-2-4-9(7)13-10/h1-5H,6H2

Upstream product

• 1646-26-0 1-(benzo[b]furan-2-yl)ethanone 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 158663-82-2 1-Benzofuran-2-yl-2-[(2-benzofuran-2-yl-2-hydroxy-ethyl)-benzyl-amino]-ethanone 
• 76007-18-6 2-N-methylanilinoacetylbenzofuran 
• 5149-69-9 3-(1-benzofuran-2-yl)-3-oxopropanenitrile 
• 571207-64-2 7-(2-benzo[b]furan-2-yl-2-oxoethoxy)-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone 
• 119678-66-9 (R)‐1‐(benzofuran‐2‐yl)ethanol 
• 324761-15-1 (S)‐1‐(benzofuran‐2‐yl)ethanol 

Relevant articles and documents

Synthesis and anticoccidial activity of 3-(2-(benzofuran)-2-yl)-2- oxoethylquinazolinone derivatives

In order to develop novel and effective anticoccidial compounds, a series of 3-(2-(benzofuran)-2-yl)-2-oxoethylquinazolinone derivatives were designed, synthesised and evaluated as potential anticoccidial drugs. The structures of these compounds were characterised by 1H NMR, IR, HRMS spectra and elemental analysis. These compounds were tested for anticoccidial activities against Eimeria tenella according to the anticoccidial index method. 6-Chloro-3-(2-(benzofuran-2-yl)-2-oxoethyl) quinazolin-4-(3H)-one exhibited significant anticoccidial activities in the chicken's diet with a dose of 18 mg kg-1.

Synthesis, reactivity and biological activity of novel bisbenzofuran-2-yl- methanone derivatives

Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields.

2-Mercapto-4,6-disubstituted nicotinonitriles: versatile precursors for novel mono- and bis[thienopyridines]

A series of novel thieno[2,3-b]pyridines were prepared from the reaction of the appropriate bromoacetylbenzofurans or bromoacetylbenzothiazole with the corresponding pyridinethione derivatives in ethanolic sodium ethoxide at reflux. Moreover, new bis(thieno[2,3-b]pyridine) derivatives have also been synthesized by the reaction of the appropriate bis-bromoacetyl derivatives with the corresponding pyridinethiones in the presence of sodium ethoxide. Attempts to synthesize the target bis(thieno[2,3-b]pyridine) derivatives by bis-alkylation of the corresponding (thieno[2,3-b]pyridin-2-yl)(hydroxyphenyl)methanone with the appropriate dihaloalkanes using a mild base were unsuccessful.

Novel benzofuran derivatives: Synthesis and antitumor activity

A series of new benzofuran derivatives 3a-f, 5a-e containing a heterocyclic substituent linked to benzofuran nucleus at C-2 were synthesized as potential antitumor agents. These products were synthesized starting with 2-bromoacetylbenzofuran 1. The structures of all compounds were established on the basis of analytical and spectral data. The synthesized compounds were tested against human liver carcinoma cell line (HEPG2) and all were more potent than the comparative standard (5-flurouracil). Compound 3f was the most active (IC50 = 12.4μg/mL).

Synthesis of benzofuran derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase: Effects on cell toxicity and osteoblast-induced mineralization

Tissue-nonspecific alkaline phosphatase (TNAP) by hydrolyzing pyrophosphate, an inhibitor of apatite formation, promotes extracellular matrix calcification during bone formation and growth, as well as during ectopic calcification under pathological conditions. TNAP is a target for the treatment of soft tissue pathological ossification. We synthesized a series of benzofuran derivatives. Among these, SMA14, displayed TNAP activity better than levamisole. SMA14 was found to be not toxic at doses of up to 40 μM in osteoblast-like Saos-2 cells and primary osteoblasts. As probed by Alizarin Red staining, this compound inhibited mineral formation in murine primary osteoblast and in osteoblast-like Saos-2 cells.

α-Nitrosostyrenes as Three-Atom Units for the (3+1) Cyclization Reaction: Facile Access to 2,3-Dihydrodiazete N-Oxides and Their Diversified Synthetic Conversions

An unprecedented (3+1) cyclization of α-nitrosostyrenes, generated in situ from α-bromooximes, and N-tosyloxycarbamates was developed, which enables the synthesis of a range of structurally unique and hitherto unexplored 2,3-dihydrodiazete N-oxides in mod

Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives

Abstract: A new series of glycosyl benzofuranylthiazole derivatives were designed, synthesized, characterized, and evaluated as potential candidates to treat Alzheimer’s disease. The compounds have been synthesized by the cyclocondensation of glycosyl thiourea with a variety of 2-(bromoacetyl)benzofurans. The reaction conditions have been optimized, and good yields (79–95%) have been obtained. The synthesized compounds showed different degrees of cholinesterase inhibitory activity.

Based on isoxazole substitution of benzamide derivatives and anti-prostate cancer drug applications

The present invention discloses a class (I), formula (II) structure based on isoxazole substituted benzamide derivatives and antiprostate cancer drug applications, such isoxazole substituted benzamide derivatives, can effectively inhibit the activity of a

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Synthesis of novel scaffolds based on thiazole or triazolothiadiazine linked to benzofuran or benzo[d]thiazole moieties as new hybrid molecules

A synthesis of novel hybrid molecules containing thiazole or bis(thiazoles) each bearing benzofuran and/or benzo[d]thiazole moieties by the reaction of the appropriate thioamide derivatives with the corresponding bis-bromoacetyl derivatives is reported. M