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

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

• 3034-05-7 6-chloroflavanone 
• 5067-25-4 1-(2-hydroxy-5-chlorophenyl)-3-phenylpropane-1,3-dione 
• 1350477-58-5 4-chloro-2-(3-phenylpropynoyl)phenol 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 635-93-8 5-chlorosalicyclaldehyde 
• 1262020-27-8 4-chloro-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol 
• 201230-82-2 carbon monoxide 
• 71643-66-8 4-chloro-2-iodo phenol 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 100-52-7 benzaldehyde 
• 7436-90-0 2,2-dibromostyrene 
• 70-11-1 α-bromoacetophenone 
• 932-87-6 1-Bromo-2-phenylacetylene 

Downstream Products

• 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 
• 1375533-50-8 diethyl (6-chloro-4-oxo-2-phenyl-4H-chromen-3-yl)phosphonate 

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

Dehydrogenation of flavanones to flavones using thallium(III) acetate(TTA)

A facile conversion of flavanones to flavones by dehydrogenation of the former using thallium(III) acetate is described.

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.

Wells-Dawson heteropolyacid as reusable catalyst for sustainable synthesis of flavones

The behavior of Wells-Dawson (H6P2W 18O62·24H2O, WD) acid, both bulk and supported on silica, for the cyclodehydration reaction of 1-(2-hydroxyphenyl)-3- phenyl-1,3-propanedione to obtain flavone was studied in heterogeneous conditions, using toluene as solvent. Catalytic experiences with bulk and supported catalysts with different WD acid loadings and reuse of the catalysts were done. The catalytic activity of supported catalysts was higher than that of the bulk catalyst, and their activity was almost constant after three reaction cycles. The following reaction conditions: reflux toluene and 1% mmol of WD supported on silica (0.4 g WD acid by gram of silica) were used for the preparation of five flavones. Yields above 85% were obtained in 4-5 h.

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.

Hypervalent iodine oxidation of flavanones: A new synthesis of methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates by 1,2-aryl shift

Flavanones (1), on oxidation with (diacetoxyiodo)benzene-sulfuric acid (DIB-H2SO4) or (hydroxy(tosyloxy)iodo)benzene (HTIB) in trimethyl orthoformate, undergo facile ring contraction by 1,2-aryl shift, thereby yielding methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates (4) as major products (40-80%). cis-3-Methoxyflavanones (5) and flavones (3) are the minor products formed in variable ratios.

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.]

A very simple solvent-free method for the synthesis of 2-arylchromones using KHSO4 as a recyclable catalyst

An efficient and solvent-free procedure for the synthesis of flavones using KHSO4 as a recyclable catalyst is described. The methodology represents an environmentally friendly process in comprehensive consideration compared with other catalytic systems listed in publications. This method provides a clean, simple, solvent-free reaction and useful alternatives to prepare flavones and chromones. The use of KHSO4 catalyst provides excellent yields, also leading to an easy separation and recovery of the catalysts, which allows both low environmental impact and low cost. Other green advantages of the method are the low formation of wastes and the replacement of corrosive, soluble mineral acids.

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.

Ru(II)-catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes

The Ru(ii)-catalyzed C-H activation and annulation reaction of salicylaldehydes and disubstituted alkynes affords chromones in high yields. This reaction also works with terminal alkynes and tolerates a wide range of sensitive functional groups. The selectivity pattern of this Ru(ii)-catalyzed annulation reaction is different from the known Au(i), Rh(iii)-catalyzed annulation reactions of salicylaldehydes and terminal alkynes.