2204-33-3

Basic information

• Product Name: (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE
• Synonyms: (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE;1-(4-CHLOROPHENYL)-5-PHENYL-PENTA-2,4-DIEN-1-ONE;NSC 159054;NSC 687738;1-(4-Chlorophenyl)-5-phenyl-2,4-pentadien-1-one
• CAS NO: 2204-33-3
• Molecular Formula: C₁₇H₁₃ClO
• Molecular Weight: 268.74
• Mol File: 2204-33-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 425.7°C at 760 mmHg
• Flash Point: 242.1°C
• Appearance: /
• Density: 1.176g/cm³
• Vapor Pressure: 1.87E-07mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE(2204-33-3)
• EPA Substance Registry System: (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE(2204-33-3)

Safety Data

• Hazardous Substances Data: 2204-33-3(Hazardous Substances Data)

Usage

Description

(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is a type of chalcone, an organic compound characterized by alternating double and single carbon-carbon bonds. This specific chalcone features a phenyl group and a chlorophenyl group attached to a central carbon chain, and is known for its potential biological activities and use in organic synthesis.

Uses

Used in Organic Synthesis:
(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is used as a starting material in the synthesis of various pharmaceuticals and functional materials due to its unique molecular structure and reactivity.
Used in Pharmaceutical Industry:
(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is used as a precursor for the development of new drugs, leveraging its potential biological activities such as antimicrobial, anticancer, and anti-inflammatory properties.
Used in Antimicrobial Applications:
In the field of antimicrobials, (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is utilized for its ability to combat microbial infections, providing a potential alternative to conventional antibiotics.
Used in Anti-inflammatory Applications:
(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is employed as an anti-inflammatory agent, potentially reducing inflammation and associated symptoms in various conditions.
Used in Anticancer Applications:
In oncology, (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is used for its potential to inhibit cancer cell growth and proliferation, offering a novel approach to cancer treatment.

InChI:InChI=1/C17H13ClO/c18-16-12-10-15(11-13-16)17(19)9-5-4-8-14-6-2-1-3-7-14/h1-13H

Upstream product

• 99-91-2 para-chloroacetophenone 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 300-57-2 allylbenzene 
• 676486-15-0 1-(4-chlorophenyl)-2-(dimethyl(oxo)-λ⁶-sulfanylidene)ethan-1-one 
• 108-86-1 bromobenzene 

Downstream Products

• 1234704-12-1 (R,E)-1-(4-chlorophenyl)-3-(nitromethyl)-5-phenylpent-4-en-1-one 
• 1239279-02-7 (S,E)-2-[1-(4-chlorophenyl)-1-oxo-5-phenylpent-4-en-3-yl]malononitrile 
• 1415681-06-9 methyl 4'-chloro-3-phenethyl-[1,1'-biphenyl]-4-carboxylate 
• 1438403-25-8 (3R,4E)-1-(4-chlorophenyl)-3-methyl-5-phenylpent-4-en-1-one 
• 54006-60-9 5-(4-chloro-phenyl)-1-phenyl-3-styryl-4,5-dihydro-1H-pyrazole 

Relevant articles and documents

Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking

Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.

Antibacterial & antitubercular activities of cinnamylideneacetophenones

Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory

Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids

In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.