1849-59-8

Basic information

• Product Name: 2-(3-chlorophenyl)-2,3-dihydro-4H-chromen-4-one
• Synonyms: 3'-Chloroflavanone; 4H-1-Benzopyran-4-one, 2-(3-chlorophenyl)-2,3-dihydro-
• CAS NO: 1849-59-8
• Molecular Formula: C₁₅H₁₁ClO₂
• Molecular Weight: 258.6996
• Mol File: 1849-59-8.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 411.1°C at 760 mmHg
• Flash Point: 172.5°C
• Density: 1.293g/cm³
• Vapor Pressure: 5.75E-07mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 2-(3-chlorophenyl)-2,3-dihydro-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-chlorophenyl)-2,3-dihydro-4H-chromen-4-one(1849-59-8)
• EPA Substance Registry System: 2-(3-chlorophenyl)-2,3-dihydro-4H-chromen-4-one(1849-59-8)

Safety Data

• Hazardous Substances Data: 1849-59-8(Hazardous Substances Data)

Usage

Class

Chromenones

Derivation

Derived from chromene

Pharmaceutical applications

Anti-inflammatory, anti-tumor, antioxidant, and anti-diabetic properties

Potential use

Treatment of neurodegenerative diseases

Research interest

Drug development and medicinal chemistry

Upstream product

• 108440-16-0 (2E)-3-(3-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 491-38-3 1-benzopyran-4(4H)-one 
• 63503-60-6 3-chlorophenylboronic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 108440-16-0 1-(2-hydroxyphenyl)-3-(3-chlorophenyl)prop-2-en-1-one 
• 766-83-6 m-chlorophenylacetylene 
• 90-02-8 salicylaldehyde 

Downstream Products

• 67765-46-2 3'-Chlor-β-flavanol 
• 1849-61-2 3'-Chloroflavone 
• 534569-42-1 C₁₆H₁₄ClN₃O₂ 
• 108440-16-0 (2E)-3-(3-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Synthesis, crystal structure and antitumour activity evaluation of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives

A series of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives were synthesised through Knoevenagel condensation of substituted flavanones with thiazolidine-2,4-dione in ethanol in the presence of piperidine. The mechanism of the reaction was proposed. All synthesised compounds were characterised by IR, 1H NMR, 13C NMR, HRMS, and elemental analysis. The structure of 2-(3-chlorophenyl)-1H-thieno[2,3-c]chromen-4(2H)-one was confirmed by a single crystal X-ray diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one had moderate to good activity against A549, BGC-823, HCT116 and MDA-MB-453 cancer cell lines, and 2-(3,4-dimethoxyphenyl)-1H-thieno[2,3-c]chromen-4(2H)-one displayed similar activity against these four kinds of cancer cells compared with the reference drug.