10420-73-2

Basic information

• Product Name: 6-CHLOROFLAVONE
• Synonyms: 6-CHLOROFLAVONE;6-CHLORO-2-PHENYL-4H-CHROMEN-4-ONE;6-CHLOROFLAVONE 98%;2-Phenyl-6-chloro-4H-1-benzopyran-4-one;6-Chloro-2-(phenyl)-4H-1-benzopyran-4-one;6-Chloro-2-phenyl-4H-1-benzopyran-4-one;MRS-1131;6-Chloroflavone,98%
• CAS NO: 10420-73-2
• Molecular Formula: C₁₅H₉ClO₂
• Molecular Weight: 256.68
• Product Categories: Mono-substituted Flavones;Benzopyrans;BenzopyransHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 10420-73-2.mol
• Article Data: 54

Chemical Properties

• Melting Point: 183-185 °C(lit.)
• Boiling Point: 408.8°Cat760mmHg
• Flash Point: 173.1°C
• Appearance: /
• Density: 1.342g/cm³
• Vapor Pressure: 6.82E-07mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 6-CHLOROFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROFLAVONE(10420-73-2)
• EPA Substance Registry System: 6-CHLOROFLAVONE(10420-73-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 10420-73-2(Hazardous Substances Data)

Usage

Chemical Properties

pink crystalline powder

InChI:InChI=1/C15H9ClO2/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-9H

Upstream product

• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 315241-28-2 C₁₄H₉O₄ClC₆H₁₄Si 
• 1301225-14-8 C₁₅H₁₀BrClO₂ 
• 27007-53-0 methyl-2-bromo-5-chlorobenzoate 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 635-93-8 5-chlorosalicyclaldehyde 
• 63888-21-1 benzyl 3-phenyl-2-propynoate 
• 106-48-9 4-chloro-phenol 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 131948-09-9 2'-acetoxy-α-bromo-5'-chloro-β-methoxydihydrochalcone 
• 131948-14-6 2'-acetoxy-5'-chlorochalcone dibromide 
• 3034-05-7 6-chloroflavanone 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 

Downstream Products

• 1375533-50-8 diethyl (6-chloro-4-oxo-2-phenyl-4H-chromen-3-yl)phosphonate 
• 1644565-54-7 6-((4-chlorophenyl)amino)-2-phenyl-4H-chromen-4-one 
• 99698-76-7 5-(5-Chloro-2-methoxyphenyl)-7-phenyl-2,3-dihydro-1H-1,4-diazepine 
• 93986-79-9 6-chloro-3-hydroxy-2-phenyl-4-oxo-4H-1-benzopyran 
• 13179-00-5 MRS 1088 
• 99698-70-1 5-(5-Chloro-2-hydroxyphenyl)-7-phenyl-2,3-dihydro-1H-1,4-diazepine 

Relevant articles and documents

Palladium-catalyzed carbonylation reaction of aryl bromides with 2-hydroxyacetophenones to form flavones

Flavone of the month: A general and efficient method for the palladium-catalyzed carbonylative synthesis of flavones has been developed (see scheme). Starting from aryl bromides and 2-hydroxyacetophenones, the corresponding flavones have been isolated in good yields. Copyright

Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes

The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.

CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones

An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.

An efficient TBHP/TBAI-mediated protocol for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation

Abstract: A transition metal-free and efficient TBHP/TBAI-mediated protocol has been developed for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation. It proceeds in the presence of a catalytic amount of tetrabutylammonium iodide and oxidant tert-butyl hydroperoxide (TBHP, 5–6 M in decane) to afford the corresponding products in good to excellent yields. Furthermore, it has been observed that an increase in the concentration of TBHP to 30 mol % drastically increases the yield of 4H-chromen-4-ones, any further increase will lead to a decrease in percent yield. The mechanism of this reaction involves the generation of tertiary butoxide radical initially which by oxidative single-electron transformation is converted to iodochroman-4-one. Later the hydrogen iodide is removed from iodochroman-4-one to give the desired product, i.e. 4H-chromen-4-ones. Moreover, this is a rare example of the n-Bu4NI/TBHP-mediated C–C bond through dehydrogenative reaction. Graphic abstract: [Figure not available: see fulltext.]

Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides

Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.

Microwave assisted efficient synthesis of flavone using ZnO nanoparticles as promoter under solvent-free conditions

A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.

Single Step Synthetic Method for Homoisoflavonoids and Flavones

The present invention relates to a one-pot synthesis method of homoisoflavonoid derivatives and flavone derivatives. By conducting a reaction of salicylicaldehyde and arylalkynoic acid in the presence of a ruthenium catalyst and a base, homoisoflavonoids and flavones can be selectively obtained through a single step (one-pot). Therefore, a synthesis method of the present invention is a simple/disposable selective metal catalyst synthesis method, which can be used to manufacture a plurality of bioactive materials.COPYRIGHT KIPO 2019