10420-75-4

Basic information

• Product Name: 4'-chloroflavone
• Synonyms: 4H-1-Benzopyran-4-one, 2-(4-chlorophenyl)-
• CAS NO: 10420-75-4
• Molecular Formula: C₁₅H₉ClO₂
• Molecular Weight: 256.68
• Mol File: 10420-75-4.mol
• Article Data: 92

Chemical Properties

• Boiling Point: 391°Cat760mmHg
• Flash Point: 163.7°C
• Appearance: /
• Density: 1.342g/cm³
• CAS DataBase Reference: 4'-chloroflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-chloroflavone(10420-75-4)
• EPA Substance Registry System: 4'-chloroflavone(10420-75-4)

Safety Data

• Hazardous Substances Data: 10420-75-4(Hazardous Substances Data)

Usage

Description

4'-chloroflavone, a flavonoid derivative with the molecular formula C15H9ClO2, is characterized by a chlorine substituent at the 4' position on the B-ring. This chemical compound has garnered attention for its potential anti-inflammatory and anti-cancer properties, making it a subject of ongoing research for its therapeutic applications in various diseases.

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

• 43016-14-4 4-chloro-2'-hydroxychalcone dibromide 
• 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 
• 1351986-57-6 1-[2-(4-chlorobenzoyloxy)-phenyl]-2-bromoethanone 
• 1351986-51-0 2-(4-chlorobenzoyloxy)benzoylmethyltriphenylphosphonium bromide 
• 67-56-1 methanol 
• 65599-34-0 1-(4-chloro-phenyl)-3-(2-hydroxy-phenyl)-propane-1,3-dione 
• 52923-39-4 (E)-2'-hydroxy-4-chlorochalcone 
• 3033-96-3 4-chloro-2'-hydroxychalcone 
• 22105-07-3 3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 

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 
• 1373355-48-6 (E)-4’-chloro-3-styrylflavone 
• 143468-16-0 2-(4-Chloro-phenyl)-3-nitro-chromen-4-one 
• 82340-48-5 C₁₇H₁₂ClNO₃ 
• 79495-23-1 Acetic acid 2-[3-(4-chloro-phenyl)-isoxazol-5-yl]-phenyl ester 
• 19275-70-8 3-Hydroxy-4'-chloroflavone 

Relevant articles and documents

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.

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.

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.

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

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.

A Facile Preparation of Flavones Using Nonaqueous Cation-Exchange Resin

Flavone was prepared from 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione by using nonaqueous cation exchange resin in a nearly quantitative yield.Of several reaction media, isopropyl alcohol gave the best result.Eight substituted flavones were also synthesized from the corresponding diketones in satisfactory yields.

Experimental and theoretical insights into the photophysical and electrochemical properties of flavone-based hydrazones

A small library of flavone-based hydrazones has been designed, synthesized and characterized. In this context, thirteen flavone hydrazones (3a-3 m) were synthesized by the acid-catalyzed condensation of flavone with 2,4-dinitrophenylhydrazine (2,4-DNPH) and characterized by different spectral techniques (IR, UV–Vis, NMR and mass spectrometry). The electrochemical, photophysical and theoretical investigations of such type of compounds are hitherto unknown. The electrochemical behavior of these hydrazones at a platinum electrode has been analyzed by cyclic voltammetry (CV) and was investigated at 200, 100 and 40 mVs?1 in acetonitrile (CH3CN). These hydrazones showed a quasi-reversible redox reaction. The oxidation–reduction reactive sites of these derivatives were located via geometry optimization using density functional theory (DFT) at the B3LYP/3–21 g in the Guassian-09 level of theory. Moreover, the target compounds exhibited interesting fluorescent properties. Owing to their excellent photophysical and redox results, a detailed structure-property relationship was established to assess the substituents impact and their position on the physicochemical and electronic properties. All the experimental results were in accordance with the computational studies.

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.