10420-75-4

Usage

Uses

Used in Pharmaceutical Industry:
4'-chloroflavone is used as an anti-inflammatory agent for its ability to inhibit the production of inflammatory mediators and cytokines, which may contribute to the treatment of inflammatory diseases.
Used in Oncology:
4'-chloroflavone is used as an anti-cancer agent due to its antiproliferative effects on cancer cells. It induces apoptosis and cell cycle arrest, which can potentially lead to the development of new therapeutic strategies for cancer treatment.

Upstream product

• 65599-34-0 1-(4-chloro-phenyl)-3-(2-hydroxy-phenyl)-propane-1,3-dione 
• 93514-36-4 4'-chloroflavanone 
• 149-73-5 trimethyl orthoformate 
• 67139-33-7 Methanesulfonic acid (2R,3R)-2-(4-chloro-phenyl)-4-oxo-chroman-3-yl ester 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 315241-18-0 C₁₄H₉O₄ClC₆H₁₄Si 
• 118-93-4 o-hydroxyacetophenone 
• 122-01-0 4-chloro-benzoyl chloride 
• 1221190-13-1 C₁₅H₁₀BrClO₂ 
• 1301225-23-9 C₁₅H₁₀Cl₂O₂ 
• 610-96-8 methyl chlorobenzoate 
• 99-91-2 para-chloroacetophenone 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 132971-93-8 2'-hydroxy-4-chlorochalcone 

Downstream Products

• 128814-94-8 7a-(4-Chloro-phenyl)-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one 
• 134051-33-5 1a,7a-Dihydro-1a-(4-chlorophenyl)-7H-oxireno<1>benzopyran-7-one 
• 16074-52-5 4'-chloro-4-thionoflavone 
• 82340-46-3 2-(4-Chloro-phenyl)-chromen-4-one oxime 
• 19743-21-6 5-(2-hydroxyphenyl)-3-(4-chloro-phenyl)-isoxazole 
• 19275-70-8 3-Hydroxy-4'-chloroflavone 
• 79495-23-1 Acetic acid 2-[3-(4-chloro-phenyl)-isoxazol-5-yl]-phenyl ester 
• 82340-48-5 C₁₇H₁₂ClNO₃ 
• 143468-16-0 2-(4-Chloro-phenyl)-3-nitro-chromen-4-one 
• 1373355-48-6 (E)-4’-chloro-3-styrylflavone 

Relevant academic research and scientific papers

A 'one pot' synthesis of 2-aryl-4H-1-benzopyran-4-ones under coupled microwave phase transfer catalysis (PTC) and ultrasonic irradiation PTC

(Chemical Equation Presented) A 'one pot' synthesis of 2-aryl-4H-1- benzopyran-4-ones (3a-3f) is being reported. A mixture of o-hydroxyacetophenone, aroyl chloride, powdered n-tetrabutylammonium hydrogensulphate (n-TBAHSO 4) and potassium hydroxide (KOH) were either irradiated by microwaves or sonicated in an ultrasonic cleaning bath to afford flavones directly. On the contrary, conventional liquid-liquid Phase Transfer Catalysis (PTC) using benzene as organic phase and aqueous KOH as the second phase afforded first β-diketones in accordance with Baker-Venkataraman synthesis which upon cyclization by p-toluenesulphonic acid (p-TSA) gave desired flavones in the next step. PTC coupled with microwaves or ultrasound show enhanced yields, the clean reaction conditions require less time, and have easier workup protocol. All synthesized compounds were characterized by their Proton Magnetic Resonance (PMR), IR, FAB Mass and elemental analyses.

Silica-PCL5: An efficient and reusable catalyst for cyclodehydration of 1, 3-diketones to flavones

Silica-PCl5 was employed as efficient solid acid catalyst for conversion of 1, 3-diketones to flavones under solventfree condition. Reaction is simple, efficient with easy work up and the catalyst is recyclable.

A facile synthesis of flavones catalysed by gallium(III) triflate

Ga(OTf)3 was explored as a novel catalyst for the cyclisation of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in nitromethane to flavones with excellent yields.

Gold Nanoparticles Supported on a Layered Double Hydroxide as Efficient Catalysts for the One-Pot Synthesis of Flavones

Flavones are a class of natural products with diverse biological activities and have frequently been synthesized by step-by-step procedures using stoichiometric amounts of reagents. Herein, a catalytic one-pot procedure for the synthesis of flavone and its derivatives is developed. In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various kinds of flavones can be synthesized starting from 2′-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). The present one-pot procedure consists of a sequence of several reactions, and Au/LDH can catalyze all these different types of reactions. The catalysis is shown to be truly heterogeneous, and Au/LDH can be readily recovered and reused. Go for gold: In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various flavones were obtained from the corresponding 2′-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). All three (four) steps of this one-pot process are catalyzed by Au/LDH in a truly heterogeneous fashion.

Ultrasonic-assisted synthesis of flavones by oxidative cyclization of 2′-hydroxychalcones using iodine monochloride

This paper presents an efficient methodology for the synthesis of flavones via the oxidative cyclization of 2′-hydroxychalcones in the presence of iodine monochloride with DMSO under ultrasound irradiation. Ultrasonic irradiation enhances the cyclization reaction and leads to reduced reaction time at lower reaction temperatures while generating flavones with high yields.

An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide

A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.

Cyclization of 2'-hydroxychalcones to flavones using ammonium iodide as an iodine source - An eco-friendly approach

Ammonium iodide on exposure to air decomposes to ammonia and iodine. The in situ generated iodine was used for the cyclization of 2'-hydroxychalcones to the corresponding flavones under solvent-free conditions in good to excellent yields. This method could serve as an attractive alternative to the existing methods for synthesis of flavones and the use of toxic molecular iodine is avoided. Copyright

The Direct Preparation of Flavones from 2'-Hydroxychalcones Using Disulfides

Flavone was obtained by a reaction of 2'-hydroxychalcone with disulfides in good yield.Among several disulfides, diphenyl disulfide gave the best result.Under the same conditions, some flavones were obtained from the corresponding 2'-hydroxychalcones in satisfactory yields.

Syntheses of flavones via the iodine-mediated oxidative cyclization of 1,3-diphenylprop-2-en-1-ones

The syntheses of flavones from 1,3-diphenylporp-2-ene-1-ones are described. When 1,3-diphenylprop-2-en-1-ones were heated with iodine in triethylene glycol, oxidative cyclization underwent to obtain flavones in good yields.

Water-mediated phosphorylative cyclodehydrogenation: An efficient preparation of flavones and flavanones

A new synthetic strategy utilizing POCl3-water for the conversion of 2′-hydroxychalcones to flavanones and flavones has been developed. The reagent efficiently promoted one-pot conversion of 2′-hydroxychalcones to flavones through flavanones involving cyclization and oxidative dehydrogenation. By changing the stoichiometery of the reagents, the reaction can be tuned to generate either flavanone or flavone. The developed protocol was found to be applicable for a variety of 2′-hydroxychalcones.