5332-98-9

Basic information

• Product Name: (1E)-1,5-bis(2-chlorophenyl)penta-1,4-dien-3-one
• CAS NO: 5332-98-9
• Molecular Formula: C₁₇H₁₂Cl₂O
• Molecular Weight: 303.1826
• Mol File: 5332-98-9.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 459.6°C at 760 mmHg
• Flash Point: 193.4°C
• Density: 1.28g/cm³
• Vapor Pressure: 1.25E-08mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: (1E)-1,5-bis(2-chlorophenyl)penta-1,4-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1,5-bis(2-chlorophenyl)penta-1,4-dien-3-one(5332-98-9)
• EPA Substance Registry System: (1E)-1,5-bis(2-chlorophenyl)penta-1,4-dien-3-one(5332-98-9)

Safety Data

• Hazardous Substances Data: 5332-98-9(Hazardous Substances Data)

Usage

General Description

(1E)-1,5-bis(2-chlorophenyl)penta-1,4-dien-3-one is a chemical compound that falls under the category of α,β-unsaturated ketones. It is a yellow crystalline solid with a chemical formula of C18H12Cl2O. (1E)-1,5-bis(2-chlorophenyl)penta-1,4-dien-3-one is used in organic synthesis and pharmaceutical research due to its potential biological activities. It has been studied for its antitumor, antiviral, and anti-inflammatory properties. Additionally, it has shown potential as a selective estrogen receptor modulator. However, its precise applications and effects are still under investigation, and further research is needed to fully understand its potential uses and properties.

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 123-54-6 acetylacetone 
• 67-64-1 acetone 
• 91574-67-3 2-chlorobenzalacetone 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 2256-20-4 5-(2-Chlor-phenyl)-3-(2-chlor-styryl)-1-phenyl-Δ²-pyrazolin 
• 181520-04-7 7,11-bis(2-chlorophenyl)-3-thioxo-2,4-diazaspiro[5.5]undecane-1,5,9-trione 
• 150160-32-0 7,11-bis(2-chlorophenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone 
• 1217056-10-4 C₂₀H₁₅Cl₂NO₄ 
• 1290622-29-5 4-nitro-3,5-di(2-chlorophenyl) cyclohexanone 
• 122228-65-3 bis (4-o-chlorophenyl-2-pyrazolin-3-yl) ketone 

Relevant articles and documents

Synthesis and Cytotoxicity of Diarylpentanoids against Sensitive CCRF-CEM and Multidrug-Resistant CEM/ADR5000 Leukemia Cells

This article described the synthesis and biological investigation of a series of symmetric diarylpentanoids, characterized by a dienone moiety and by a different pattern of substitution on the two phenyl rings. The series of compounds 1a–p were tested aga

Electrospray ionization tandem mass spectrometry of monoketone curcuminoids

Rationale: Although monoketone curcuminoids (MKCs) have been largely investigated due to their biological activities, data on the gas-phase fragmentation reactions of protonated MKCs under collision-induced dissociation (CID) conditions are still scarce. Here, we combined electrospray ionization tandem mass spectrometry (ESI-MS/MS) data, multiple-stage mass spectrometry (MSn), deuterium exchange experiments, accurate-mass data, and thermochemical data estimated by computational chemistry to elucidate and to rationalize the fragmentation pathways of eleven synthetic MKCs. Methods: The MKCs were synthesized by Claisen-Schmidt condensation under basic (1–9) or acidic (10–11) conditions. ESI-CID-MS/MS analyses and deuterium-exchange experiments were carried out on a triple quadrupole mass spectrometer. MSn analyses on an ion trap mass spectrometer helped to elucidate the fragmentation pathways. Accurate-mass data and thermochemical data, obtained at the B3LYP/6–31+G(d,p) level of theory, were used to support the ion structures. Results: The most intense product ions were the benzyl ions ([C7H2R1R2R3R4R5]+) and the acylium ions ([M + H ? C8H3R1R2R3R4R5]+), which originated directly from the precursor ion as a result of two competitive hydrogen rearrangements. Product ions [M + H – H2O]+ and [M + H ? C6HR1R2R3R4R5]+, which are formed after Nazarov cyclization, were also common to all the analyzed compounds. In addition, ?Br and ?Cl eliminations were diagnostic for the presence of these halogen atoms at the aromatic ring, whereas ?CH3 eliminations were useful to identify the methyl and methoxy groups attached to this same ring. Nazarov cyclization in the gas phase occurred for all the investigated MKCs and did not depend on the presence of the hydroxyl group at the aromatic ring. However, the presence and the position of a hydroxyl group at the aromatic rings played a key role in the Nazarov cyclization mechanism. Conclusions: Our results reinforce some aspects of the fragmentation pathways previously published for 1,5-bis-(2-methoxyphenyl)-1,4-pentadien-3-one and 1,5-bis-(2-hydroxyphenyl)-1,4-pentadien-3-one. The alternative fragmentation mechanism proposed herein can explain the fragmentation of a wider diversity of monoketone curcuminoids.

Synthesis of 4,5,6,7-tetrahydrobenzoxazol-2-ones by a highly regioselective Diels-Alder cycloaddition of exo-oxazolidin-2-one dienes with chalcones

The synthesis of novel of 4,5,6,7-tetrahydrobenzoxazol-2-ones is herein reported. They were obtained in moderate to good yields by a highly regio- and stereoselective Diels-Alder cycloaddition of N-substituted exo-oxazolidin-2-one dienes with chalcones or bis-chalcones as dienophiles.