22252-16-0

Basic information

• Product Name: (E)-β-(4-Chlorophenyl)acrylophenone
• Synonyms: (E)-1-Phenyl-3-(4-chlorophenyl)-2-propen-1-one;(E)-4-Chlorochalcone;(E)-4-Chloro-β-benzoylstyrene;(E)-β-(4-Chlorophenyl)acrylophenone;4-Chloro-trans-chalcone;(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one
• CAS NO: 22252-16-0
• Molecular Formula: C₁₅H₁₁ClO
• Molecular Weight: 242.70024
• Mol File: 22252-16-0.mol
• Article Data: 163

Chemical Properties

• Boiling Point: 381.9°Cat760mmHg
• Flash Point: 210.3°C
• Appearance: /
• Density: 1.202g/cm³
• CAS DataBase Reference: (E)-β-(4-Chlorophenyl)acrylophenone(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-β-(4-Chlorophenyl)acrylophenone(22252-16-0)
• EPA Substance Registry System: (E)-β-(4-Chlorophenyl)acrylophenone(22252-16-0)

Safety Data

• Hazardous Substances Data: 22252-16-0(Hazardous Substances Data)

Usage

General Description

(E)-β-(4-Chlorophenyl)acrylophenone is a chemical compound with the molecular formula C15H11ClO. It is a yellow solid with a molecular weight of 244.7 g/mol. The compound is also known as Z-β-(4-Chlorophenyl)acrylophenone and is often used as a building block in organic synthesis and pharmaceutical research. It is a potent inhibitor of human cytochrome P450 3A4 and has been studied for its potential in treating cancer and inflammation. The compound is also used in the production of various drugs and pharmaceutical products. However, it is important to handle this chemical with care, as it may be hazardous to health and the environment.

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 98-86-2 acetophenone 
• 24721-26-4 (2Z)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 111873-49-5 Te-phenacyldi(n-butyl)telluronium bromide 
• 42350-78-7 (2-oxo-2-phenylethyl)triphenylarsonium bromide 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 153491-51-1 3-(4-Chloro-phenyl)-2,2,2-trimethoxy-5-phenyl-2,3-dihydro-2λ⁵-[1,2]oxaphosphole 
• 72028-22-9 diethyl 2-[1-(4-chlorophenyl)-3-oxo-3-phenylpropyl]malonate 
• 101854-87-9 trans-2-benzoyl-3-(4-chlorophenyl)aziridine 
• 70-11-1 α-bromoacetophenone 
• 83624-73-1 3-Benzoyl-2,6-bis-(4-chloro-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester 
• 22535-03-1 phenylacetyl bromide 
• 1073-67-2 4-vinylbenzyl chloride 
• 88691-45-6 (E)-[2-(4-chlorophenyl)ethenyl]trimethylsilane 

Downstream Products

• 144765-45-7 (1R*,2R*,3S*,4S*,6S*)-(+/-)-2,6-Bis-(4-chlorophenyl)-3-benzoyl-1-(4-bromophenyl)-4-hydroxy-4-phenylcyclohexanecarbonitrile 
• 129226-60-4 3-(4-Chloro-phenyl)-4-(5-methyl-4-nitro-2-phenyl-2H-pyrazol-3-yl)-1-phenyl-butan-1-one 
• 138982-96-4 3-(4-chlorophenyl)-1-phenyl-1-pentanone 
• 143968-99-4 4-(4-Chloro-phenyl)-6-phenyl-pyridin-2-ol 
• 95855-32-6 2-(4-chlorophenyl)-4-oxo-4-phenylbutanenitrile 
• 137594-15-1 4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,8,10,12-hexaene 
• 107710-40-7 Dithiocarbamic acid 1-(4-chloro-phenyl)-3-oxo-3-phenyl-propyl ester 
• 72028-26-3 3-(4-Chlorphenyl)-5-oxo-5-phenylpentansaeure 
• 80674-55-1 5-(4-Chlorphenyl)-3-hydroxy-3-phenyl-(E)-4-pentensaeure 
• 6969-01-3 ((2S,3R)-3-(4-chlorophenyl)oxiran-2-yl)(phenyl)methanone 
• 6969-01-3 ((2R,3S)-3-(4-chlorophenyl)oxiran-2-yl) (phenyl)methanone 
• 60579-19-3 5-(4-chlorophenyl)-3-phenyl-4,5-dihydroisoxazole 
• 24721-26-4 (2Z)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 61571-80-0 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one oxime 

Relevant articles and documents

A four-component Biginelli reaction: new opportunities for the synthesis of functionalized pyrimidines

[Figure not available: see fulltext.] Methyl 5-aroyl-6-aryl-4-methoxy-2-oxo(thioxo)hexahydropyrimidine-4-carboxylates were synthesized by four-component Biginelli reaction of methyl aroylpyruvate, aromatic aldehyde, urea (thiourea), and MeOH in the presence of NaHSO4. The products were obtained in moderate to high yields.

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Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones

Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).

Synthesis, characterization and biological evaluation of new 3,5-disubstituted-pyrazoline derivatives as potential anti-Mycobacterium tuberculosis H37Ra compounds

A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer-DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c–5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand– receptor interactions, and to hypothesize potential refinements for the compound.

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.