60402-30-4

Basic information

• Product Name: 4'-CHLORO-6-METHYLFLAVONE
• Synonyms: 4'-CHLORO-6-METHYLFLAVONE;AURORA KA-4460;2-(4-chlorophenyl)-6-methylchromen-4-one
• CAS NO: 60402-30-4
• Molecular Formula: C₁₆H₁₁ClO₂
• Molecular Weight: 270.71
• Mol File: 60402-30-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 196.5-197 °C
• Boiling Point: 418.5°Cat760mmHg
• Flash Point: 172.2°C
• Appearance: /
• Density: 1.304g/cm³
• Vapor Pressure: 3.27E-07mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 4'-CHLORO-6-METHYLFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORO-6-METHYLFLAVONE(60402-30-4)
• EPA Substance Registry System: 4'-CHLORO-6-METHYLFLAVONE(60402-30-4)

Safety Data

• Hazardous Substances Data: 60402-30-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H11ClO2/c1-10-2-7-15-13(8-10)14(18)9-16(19-15)11-3-5-12(17)6-4-11/h2-9H,1H3

Upstream product

• 14166-16-6 2-(4-chlorophenyl)-6-methylchroman-4-one 
• 60402-29-1 1-(4-Chloro-phenyl)-3-(2-hydroxy-5-methyl-phenyl)-propane-1,3-dione 
• 149-73-5 trimethyl orthoformate 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 4010-22-4 1-[2-(4-chlorobenzoyloxy)-5-methylphenyl]-ethanone 
• 122-01-0 4-chloro-benzoyl chloride 
• 1351986-49-6 2-(4-chlorobenzoyloxy)-5-methyl-benzoylmethyltriphenylphosphonium bromide 
• 4238-38-4 1-[2-(4-chlorobenzoyloxy)-5-methylphenyl]-2-bromoethanone 
• 74-11-3 para-chlorobenzoic acid 
• 106-44-5 p-cresol 
• 140-39-6 1-acetoxy-4-methylbenzene 
• 16635-10-2 1-(p-chlorophenyl)-3-(2-hydroxy-5-methylphenyl)prop-1-en-3-one 
• 104-88-1 4-chlorobenzaldehyde 
• 126267-43-4 (E)-3-(4-chlorophenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one 

Downstream Products

• 136764-54-0 1a,7a-Dihydro-5-methyl-1a-(4-chlorophenyl)-7H-oxireno<1>benzopyran-7-one 
• 60402-31-5 6-Bromomethyl-2-p-chlorophenylchromone 
• 1343513-06-3 2-(4-chlorophenyl)-6-((diethylamino)methyl)-4H-chromen-4-one 
• 1343513-07-4 2-(4-chlorophenyl)-6-(piperidin-1-ylmethyl)-4H-chromen-4-one 
• 1343513-08-5 2-(4-chlorophenyl)-6-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one 
• 1343513-09-6 2-(4-chlorophenyl)-6-(morpholin-4-ylmethyl)-4H-chromen-4-one 
• 1343513-10-9 2-(4-chlorophenyl)-6-(piperazin-1-ylmethyl)-4H-chromen-4-one 
• 1343513-11-0 2-(4-chlorophenyl)-6-((dimethylamino)methyl)-4H-chromen-4-one 
• 1343513-12-1 6-((1H-imidazol-1-yl)methyl)-2-(4-chlorophenyl)-4H-chromen-4-one 
• 1343513-13-2 N-((2-(4-chlorophenyl)-4-oxo-4H-chromen-6-yl)methyl)-N,N-diethylethanaminium 

Relevant articles and documents

Rapid synthesis of flavone-based monoamine oxidase (MAO) inhibitors targeting two active sites using click chemistry

A new library of flavone derivatives targeting two active sites of monoamine oxidases (“aromatic cage” and substrate cavity) were designed and synthesized using click chemistry (CuAAC reaction) between 6-N3-2-phenyl chromones (Az1–Az2) and a series of alkynes (k1–k20). Their inhibitory activities against MAO isoforms (MAO-A and MAO-B) are evaluated. Compounds with fluorine, amide bonds, or amino bonds have shown better inhibition. The most potent flavone MAO inhibitor studied is Az2k19 (1.6?μm for MAO-A, 2.1?μm for MAO-B), while Az1k15 and Az2k15 displayed better selectivity toward MAO-B (SI?>?10). Docking studies are in accordance with our hypothesis that these inhibitors are most likely located at both the substrate cavity and the “aromatic cage”. Our results show that it is considerable to develop new MAO inhibitors from C6 substitution of flavone derivatives and that these compounds are also potential for the treatment of diseases associated with MAOs.

Synthesis and biological activities of some flavones

Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coilt P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.

Investigation on the substitution effects of the flavonoids as potent anticancer agents: A structure-activity relationships study

Three series of flavonoid analogues substituted with different aminomethyl substitutions at C-6, C-7, and C-8 were designed and synthesized for the structure-activity relationship studies as potent anticancer agents. The prepared analogues were evaluated for their in vitro inhibitory activity against the growth of the hepatic cancer cell lines HepG2 and SMMC-7721. Structure-activity relationships indicated that not only the compounds with amino methyl groups were more active than those without the groups in the same series but also the compounds substituted by aminomethyl groups at position C-8 were more active than those at positions C-6 and C-7.