1744-33-8

Basic information

• Product Name: 2-(3-fluorophenyl)-4H-chromen-4-one
• CAS NO: 1744-33-8
• Molecular Formula: C₁₅H₉FO₂
• Molecular Weight: 240.2292
• Mol File: 1744-33-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 370.8°C at 760 mmHg
• Flash Point: 172°C
• Density: 1.309g/cm³
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: 2-(3-fluorophenyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-fluorophenyl)-4H-chromen-4-one(1744-33-8)
• EPA Substance Registry System: 2-(3-fluorophenyl)-4H-chromen-4-one(1744-33-8)

Safety Data

• Hazardous Substances Data: 1744-33-8(Hazardous Substances Data)

Usage

Compound group

Flavonoids.

Natural occurrence

Found in various plants.

Known properties

Antioxidant and anti-inflammatory.

Potential biological activities

Inhibition of certain enzymes, development of new drugs.

Additional potential

Fluorescent probe for metal ions.

Useful applications

Analytical and diagnostic purposes.

Fields of interest

Pharmaceuticals, biochemistry, and materials science.

Upstream product

• 456-48-4 3-Fluorobenzaldehyde 
• 1840-00-2 3-(3-fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 533-58-4 2-Iodophenol 
• 201230-82-2 carbon monoxide 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 53631-18-8 2-bromo-1-(3-fluorophenyl)ethanone 
• 90-02-8 salicylaldehyde 
• 813414-83-4 1-bromo-2-(meta-fluorophenyl)ethyne 
• 491-38-3 1-benzopyran-4(4H)-one 
• 768-35-4 3-fluorophenylboronic acid 
• 145370-30-5 3-fluoro-benzoic acid 2-acetyl-phenyl ester 
• 1711-07-5 3-fluorobenzoyl chloride 
• 118-93-4 o-hydroxyacetophenone 
• 145370-34-9 1-(3-fluoro-phenyl)-3-(2-hydroxy-phenyl)-propane-1,3-dione 

Downstream Products

• 1678-20-2 2-(3-fluorophenyl)chroman-4-one 
• 1610536-07-6 (+)-2-(3-fluorophenyl)chroman-4-one 

Relevant articles and documents

Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide

In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.

Divergent synthesis of flavones and aurones via base-controlled regioselective palladium catalyzed carbonylative cyclization

A regioselective approach for construction of 5-membered and 6-membered flavonoid is established by Pd catalyzed carbonylative cyclization of 2-iodophenol with terminal alkynes using different amine bases under mild reaction condition. The catalytic experiments found that piperazine preferentially accelerate 6-endo cyclization, and triethylamine mediated Pd catalyzed 5-exo cyclization. Under optimized reaction condition, Pd catalyzed carbonylative protocol successfully applied for the diverse structures of 39 examples in good to excellent yield and regioselectivity.

One-Pot Allan–Robinson/Friedl?nder Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes

The domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones through acetylation of 2-hydroxy-/2-aminobenzaldehydes with α-haloketones followed by intramolecular oxa-/azaheterocyclisation is reported. This method represents a new extension of the Allan–Robinson and Friedl?nder reactions, and uses N-heterocyclic-carbene catalysis to construct the target molecules in good to excellent yields: 86–95 % for the chromen-4-ones, and 83–96 % for the quinolin-4-ones. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by-product formation.