62174-08-7

Basic information

• Product Name: (E)-3-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROCHROMEN-4-ONE
• Synonyms: (E)-3-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROCHROMEN-4-ONE;3-[(E)-(4-CHLOROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE
• CAS NO: 62174-08-7
• Molecular Formula: C₁₆H₁₁ClO₂
• Molecular Weight: 270.71
• Mol File: 62174-08-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 446.8°C at 760 mmHg
• Flash Point: 186.8°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 3.53E-08mmHg at 25°C
• Refractive Index: 1.666
• CAS DataBase Reference: (E)-3-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROCHROMEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROCHROMEN-4-ONE(62174-08-7)
• EPA Substance Registry System: (E)-3-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROCHROMEN-4-ONE(62174-08-7)

Safety Data

• Hazardous Substances Data: 62174-08-7(Hazardous Substances Data)

Usage

General Description

(E)-3-(4-chlorobenzylidene)-2,3-dihydrochromen-4-one, also known as Cloroquine, is a chemical compound that belongs to the category of chromen-4-one derivatives. It is a synthetic molecule that has been studied for its potential pharmacological activities, particularly its antioxidant, anti-inflammatory, and antitumor properties. (E)-3-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROCHROMEN-4-ONE has been the focus of research for its potential therapeutic uses in treating various diseases and conditions. Its structure contains a substituted benzylidene group attached to a chromenone ring, which gives it unique chemical and biological properties. Further research is needed to fully understand the potential applications and mechanisms of action of this compound.

InChI:InChI=1/C16H11ClO2/c17-13-7-5-11(6-8-13)9-12-10-19-15-4-2-1-3-14(15)16(12)18/h1-9H,10H2/b12-9+

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 1126-20-1 2-allyloxyphenol 
• 533-58-4 2-Iodophenol 
• 103979-29-9 para-chlorocinnamyl chloride 
• 108-95-2 phenol 
• 3055-86-5 3-phenoxypropionitrile 
• 7170-38-9 3-phenoxypropanoic acid 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 114283-20-4 2-Amino-4-(4-chloro-phenyl)-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile 
• 1262616-63-6 (2'S,3S,4'R)-2'-(4-chlorophenyl)-4'-hydroxyspiro[chroman-3,3'-thiochroman]-4-one 
• 76285-74-0 3-(4-chlorobenzyl)-chroman-4-one 
• 1350889-80-3 C₃₂H₂₂Cl₂O₄ 

Relevant articles and documents

I2/TBHP mediated diastereoselective synthesis of spiroaziridines

Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible α,β-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.

Synthesis and biological evaluation of 3-benzylidene-4-chromanone derivatives as free radical scavengers and α-glucosidase inhibitors

A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 μM; 13: EC50 14 μM; 18: EC50 13 μM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 μM; 14: IC50 25 μM; 18: IC50 28 μM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

Facile condensation of aromatic aldehydes with chroman-4-ones and 1-thiochroman-4-ones catalysed by amberlyst-15 under microwave irradiation condition

Different aromatic aldehydes and cinnamaldehyde undergo crossaldol condensation with chroman-4-ones and 1-thiochroman-4-ones in the presence of amberlyst-15 under microwave irradiation in solvent free condition to afford rapidly the corresponding E-3-arylidene and E-3-cinnamylidene derivatives, respectively, in high yield. This process is simple, efficient and environmentally benign.