22966-13-8

Basic information

• Product Name: (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one
• Synonyms: 2-Propen-1-one, 3- (3-chlorophenyl)-1-phenyl-
• CAS NO: 22966-13-8
• Molecular Formula: C₁₅H₁₁ClO
• Molecular Weight: 242.7002
• Mol File: 22966-13-8.mol
• Article Data: 62

Chemical Properties

• Boiling Point: 382.6°C at 760 mmHg
• Flash Point: 210.5°C
• Density: 1.202g/cm³
• Vapor Pressure: 4.68E-06mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one(22966-13-8)
• EPA Substance Registry System: (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one(22966-13-8)

Safety Data

• Hazardous Substances Data: 22966-13-8(Hazardous Substances Data)

Usage

Description

(2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one, commonly known as chalcone, is a yellow crystalline chemical compound with a wide range of applications in various industries. It serves as a precursor for the synthesis of pharmacologically active compounds and exhibits multiple biological activities, such as antioxidant, anti-inflammatory, anti-cancer, and antimicrobial properties.

Uses

Used in Pharmaceutical Industry:
Chalcone is used as a precursor for the synthesis of various pharmacologically active compounds, making it a valuable component in drug development. Its wide range of biological activities, including antioxidant, anti-inflammatory, anti-cancer, and antimicrobial properties, contribute to its potential as a therapeutic agent for various diseases.
Used in Organic Synthesis:
Chalcone is widely used in organic synthesis and research due to its versatile chemical structure, allowing for the development of new compounds with potential applications in various fields.
Used in Production of Fluorescent and Dye Molecules:
Chalcone is utilized in the production of fluorescent and dye molecules, which have applications in various industries, such as biotechnology, diagnostics, and imaging.
Used in Food Industry:
Due to its unique properties and versatile chemical structure, chalcone has potential applications in the food industry, where it can be used to develop new food products or enhance existing ones.
Used in Cosmetic Industry:
Chalcone's potential applications in the cosmetic industry include the development of new cosmetic products or the enhancement of existing ones, thanks to its unique properties and versatile chemical structure.

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 98-86-2 acetophenone 
• 43144-52-1 2,3-dibromo-3-(3-chloro-phenyl)-1-phenyl-propan-1-one 
• 109-77-3 malononitrile 
• 98-85-1 1-Phenylethanol 
• 873-63-2 m-chlorobenzyl alcohol 
• 625-99-0 3-iodochlorobenzene 
• 84553-32-2 α-Methylenebenzyl formate 
• 100-52-7 benzaldehyde 
• 99-02-5 3'-Chloroacetophenone 
• 70-11-1 α-bromoacetophenone 
• 118-93-4 o-hydroxyacetophenone 
• 39096-24-7 3-chlorocinnamoyl chloride 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 847062-45-7 4-(3-chloro-phenyl)-2-methyl-6-phenyl-nicotinonitrile 
• 90054-40-3 5-(4-Chloro-phenyl)-3-phenyl-1H-pyridazin-4-one 
• 59807-17-9 2-amino-4-(m-chlorophenyl)-6-phenylpyrimidine 
• 143969-06-6 4-(3-Chloro-phenyl)-6-phenyl-pyridin-2-ol 
• 87116-45-8 [5-Benzoyl-2,4-bis-(3-chloro-phenyl)-tetrahydro-thiophen-3-yl]-phenyl-methanone 
• 95734-11-5 4-(3-Chloro-phenyl)-3,6-diphenyl-3,4-dihydro-1H-pyridin-2-one 
• 80824-87-9 2-[1-(3-Chloro-phenyl)-3-oxo-3-phenyl-propylsulfanyl]-benzoic acid 
• 41904-40-9 2-(3-chlorophenyl)acetaldehyde 
• 65-85-0 benzoic acid 
• 58122-03-5 3-(3-chlorophenyl)-1-phenylpropan-1-one 
• 606-86-0 1,3,3-triphenylpropan-1-one 
• 1878-65-5 3-chlorophenylacetic acid 

Relevant articles and documents

Chalcones and flavonoids as anti-tuberculosis agents

A series of flavonoids, chalcones and chalcone-like compounds were evaluated for inhibitory activity against Mycobacterium tuberculosis H37Rv. Among them, eight compounds exhibited >90% inhibition on the growth of the bacteria at a concentration of 12.5 μg/mL. Chalcones 1-(2-hydroxyphenyl)-3-(3-chlorophenyl)-2-propen-1-one (22) and 1-(2-hydroxyphenyl)-3-(3-iodophenyl)-2-propen-1-one (37) demonstrated 90 and 92% inhibition, respectively. Chalcone-like compounds (heterocyclic ring-substituted 2-propen-1-one) 1-(4-fluorophenyl)-3-(pyridin-3-yl)-2-propen-1-one (48), 1-(3-hydroxyphenyl)-3-(phenanthren-9-yl)-2-propen-1-one (49), 1-(pyridin-3-yl)-3-(phenanthen-9-yl)-2-propen-1-one (50) and 1-(furan-2-yl)-3-phenyl-2-propen-1-one (51) exhibited 98, 97, 96 and 96% inhibition, respectively. The actual minimum inhibitory concentrations (MIC), defined as the lowest concentration inhibiting 99% of the inoculum, for 22, 37, 48, 49, 50 and 51 were 20.3, 31.5, 48.3, >35.7, 6.8 and 19.2, respectively. A hydrophobic substituent on one aromatic ring, and a hydrogen-bonding group on the other aromatic ring resulted in increased anti-TB activity of the chalcones and chalcone-like compounds. Flavones and flavanones are more geometrically constrained than the corresponding chalcone analogues. The decreased activity of the flavones with respect to the chalcones may be due to the confinement of the terminal aromatic rings to the same plane.

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones

The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.