5424-03-3

Basic information

• Product Name: (2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS NO: 5424-03-3
• Molecular Formula: C₁₆H₁₃ClO₂
• Molecular Weight: 272.7262
• Mol File: 5424-03-3.mol

Chemical Properties

• Boiling Point: 427.4°C at 760 mmHg
• Flash Point: 172.3°C
• Density: 1.207g/cm³
• Vapor Pressure: 1.64E-07mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: (2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one(5424-03-3)
• EPA Substance Registry System: (2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one(5424-03-3)

Safety Data

• Hazardous Substances Data: 5424-03-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one is utilized as a reagent in organic synthesis, playing a crucial role in the formation of various complex organic molecules.
Used in Pharmaceutical Research and Drug Development:
(2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one has potential applications in pharmaceutical research and the development of new drugs, given its unique structure and functional groups that can be further modified or used as a starting point for medicinal chemistry.
Used in Biological Activity and Pharmacological Property Studies:
(2E)-3-(2-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one may possess biological activities and pharmacological properties that are of interest to researchers, warranting further investigation into its potential therapeutic uses across different medical fields.

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 108325-97-9 [4-(2-Chloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-(4-methoxy-phenyl)-methanone 
• 1058744-75-4 (R)-2-((S)-1-(2-chlorophenyl)-3-(4-methoxyphenyl)-3-oxopropyl)cyclohexanone 
• 1058744-66-3 (S)-2-((R)-1-(2-chlorophenyl)-3-(4-methoxyphenyl)-3-oxopropyl)-cyclohexanone 
• 1234670-69-9 1-(2-chlorophenyl)-3-(4-methoxyphenyl)-3-oxopropyl diethylcarbamodithioate 
• 1258526-37-2 2-(3-(2-chlorophenyl)-1-(4-methoxyphenyl)allylidene)-hydrazinecarboximidamide 
• 1268494-09-2 C₁₈H₁₇ClO₃S 
• 1311203-87-8 (4-(2-chlorophenyl)-1H-pyrrol-3-yl)(4-methoxyphenyl)methanone 
• 41841-01-4 1-(2-chlorophenyl)-2-(4-methoxyphenyl)ethane-1,2-dione 
• 76112-11-3 5-(o-Chlorophenyl)-3-(p-methoxyphenyl)isoxazole 

Relevant articles and documents

New 2-Pyrazoline and Hydrazone Derivatives as Potent and Selective Monoamine Oxidase A Inhibitors

Thirty compounds having 1-[2-(5-substituted-2-benzoxazolinone-3-yl) acetyl]-3,5-disubstitutedphenyl-2-pyrazoline structure and nine compounds having N′-(1,3-disubstitutedphenylallylidene)-2-(5-substituted-2-benzoxazolinone-3-yl)acetohydrazide skeleton wer

Synthesis method of chalcone derivative

The invention provides a synthesis method of a chalcone derivative, which comprises the following steps: adding polyphosphoric acid PPA and a solvent 1, 4-dioxane into a container, sequentially adding98% concentrated sulfuric acid, substituted benzaldehyd

Enantioselective Copper-Catalyzed 1,5-Cyanotrifluoromethylation of Vinylcyclopropanes

A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the in situ generated CF3 radical from Togni's reagent, this method offers a new solution for remote enantioselective bifunctionalization of alkenes and thus provides a straightforward way for the synthesis of chiral CF3-containing internal alkenylnitriles.

Regiospecific Aza-Michael Addition of 4-Aryl-1 H -1,2,3-triazoles to Chalcones: Synthesis of 2,4-Disubstituted 1,2,3-Triazoles in Basic Medium

A novel metal-free and base-mediated method to display the donor ability of 1,2,3-triazoles for the synthesis of 2,4-disubstituted 1,2,3-triazoles has been developed. A DABCO-promoted aza-Michael addition of 4-aryl NH-1,2,3-triazoles to α,β-unsaturated ketones (chalcones) is presented. The reactions proceeded with complete regiospecificity in a 3:1 mixture of acetonitrile and methanol at 85 °C to provide 2,4-disubstituted 1,2,3-triazoles as Michael adducts, and the addition products 1,3-diaryl-(4-aryl-2 H -1,2,3-triazol-2-yl)propan-1-ones were isolated in high yields.

An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O

Abstract: 1,3,5-triaryl-2-pyrazoline derivatives were synthesised by a condensation reaction between chalcones and phenyl hydrazine using cerium chloride heptahydrate as a catalyst. All these reactions were carried out in ethyl lactate (70%) as a green solvent. Easy and efficient work up, recyclability of solvent and catalyst are the key merits of this protocol. Graphical Abstract:: SYNOPSIS A facile protocol for the synthesis of 1,3,5-triaryl-2-pyrazolines is described. The solvent ethyl lactate, obtained from renewable sources, is biodegradable. The catalyst CeCl 3· 7 H 2O is a water-tolerant Lewis acid with low toxicity. Easy and clean work up, recyclable solvent and catalyst are merits of the protocol. The reaction works well for all systems giving good yields of the desired products.[Figure not available: see fulltext.].

Facile Microwave-assisted Synthesis of 1,3,5-Trisubstituted Pyrazoline Derivatives Incorporating Sulfonyl Moiety

We developed an environmentally benign, convenient microwave-assisted process for the construction of 1,3,5-trisubstitued pyrazolines (10a～10f, 11a～11f, 12a～12f, 13a～13f). Chalcones, as the key intermedi- ates, were obtained by the condensation of each of appropriately substituted aromatic aldehydes (1～4) with 4-substituted acetophenones (5a～5f) via a Claisen-Schmidt reaction under the action of microwave irradiation. Cyclization of the chalcones (6a～6f, 7a～7f, 8a～8f, 9a～9f) with p-toluene sulfonhydrazide af- forded 1,3,5-trisubstitued pyrazoline derivatives using microwave-assisted process in 25 min and 140 watt power in glycol. The structures of targeted compounds were established by IR, 1H NMR, MS and ele- mental analysis. The results indicate that microwave-assisted synthetic process presents advantages in terms of enhancement in rate, decrease in reaction time, clean reaction and convenient operation.

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles

LiOH·H2O in ethanol was found to be an effective reagent for the synthesis of 3,4-disubstituted pyrrole derivatives by the van Leusen method. In situ formation of chalcones from aromatic aldehydes and enolisable ketones, and their subsequent reaction with tosylmethyl isocyanide resulted in the formation and precipitation of pyrrole derivatives from the reaction medium, in good yields. The solvation effect of the polar medium facilitates the reaction. The Royal Society of Chemistry 2013.

Synthesis and in vitro antimicrobial activity of novel 2-(3-oxo-1,3- diarylpropylthio)acetic acid derivatives

A series of novel 2-(3-oxo-1,3-diarylpropylthio)acetic acid derivatives (3a-l) were prepared by base catalyzed addition of thioglycolic acid to chalcones (1a-l). The antibacterial activities of synthesized compounds were screened against human pathogenic microorganisms by employing the disk-diffusion technique. For the active compounds, also minimum inhibitory concentrations (MICs) were determined.