621-21-6

Basic information

• Product Name: 1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one
• Synonyms: 1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one;1,5-Bis(3-nitrophenyl)-1,4-pentadien-3-one;3,3'-Dinitrobenzalacetone;Bis(3-nitrostyryl) ketone;Bis[2-(3-nitrophenyl)ethenyl] ketone;1,4-Pentadien-3-one, 1,5-bis(3-nitrophenyl)-;1,4-Pentadien-3-one, 1,5-bis(m-nitrophenyl)-;1,5-Bis(m-nitrophenyl)-1,4-pentadien-3-one
• CAS NO: 621-21-6
• Molecular Formula: C₁₇H₁₂N₂O₅
• Molecular Weight: 324.28758
• EINECS: 210-672-9
• Mol File: 621-21-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 237 °C
• Boiling Point: 533.8°C at 760 mmHg
• Flash Point: 258.8°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.79E-11mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: 1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one(621-21-6)
• EPA Substance Registry System: 1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one(621-21-6)

Safety Data

• Hazardous Substances Data: 621-21-6(Hazardous Substances Data)

Usage

General Description

1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one is a chemical compound with the molecular formula C17H11N3O4. It consists of a pentadienone backbone with two 3-nitrophenyl groups attached at the 1 and 5 positions. 1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one is often used in organic synthesis and medicinal chemistry as a building block for the synthesis of various biologically active molecules. Its nitro groups make it a strong electron-withdrawing compound, which can be useful in the development of pharmaceuticals and other valuable compounds. Additionally, the conjugated system of the pentadienone backbone makes it a valuable scaffold for the development of molecules with potential biological activity.

InChI:InChI=1/C17H12N2O5/c20-17(9-7-13-3-1-5-15(11-13)18(21)22)10-8-14-4-2-6-16(12-14)19(23)24/h1-12H/b9-7-,10-8+

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 67-64-1 acetone 
• 162467-43-8 2,3,5,6-Tetrahydro-2,6-di(3-nitrophenyl)thiopyran-4-one 1,1-dioxide 
• 946-68-9 4-(3-nitrophenyl)but-3-en-2-one 
• 542-05-2 acetonedicarboxylic acid 
• 162467-33-6 2,3,5,6-Tetrahydro-2,6-di(3-nitrophenyl)thiopyran-4-one 

Downstream Products

• 882-26-8 3-nitro-β-nitrostyrene 
• 80396-67-4 1,5-bis-(3-amino-phenyl)-penta-1,4-dien-3-one 
• 162467-33-6 2,3,5,6-Tetrahydro-2,6-di(3-nitrophenyl)thiopyran-4-one 
• 24522-97-2 3,3'-Hydrazo-bis-<3-cyan-1,5-bis-(3-benzolazo-phenyl)-pentan> 
• 24522-99-4 1,5-Bis-<3-benzolazo-phenyl>-pentan-3-on 
• 24522-95-0 Tetrakis-(3-benzolazo-phenaethyl)-succinodinitril 
• 24522-94-9 3-Chlor-3'-cyan-3,3'-azo-bis-<1,5-bis-(3-benzolazo-phenyl)-pentan> 
• 24522-93-8 3-Brom-3'-cyan-3,3'-azo-bis-<1,5-bis-(3-benzolazo-phenyl)-pentan> 
• 24019-07-6 3,3'-Azo-bis-<3-cyan-1,5-bis-(3-benzolazo-phenyl)-pentan> 
• 24522-92-7 3-Cyan-3'-acetoxy-3,3'-azo-bis-<1,5-bis-(3-benzolazo-phenyl)-pentan> 
• 24522-91-6 2-{1-Nitrooxy-3-(3-phenylazo-phenyl)-1-[2-(3-phenylazo-phenyl)-ethyl]-propylazo}-4-(3-phenylazo-phenyl)-2-[2-(3-phenylazo-phenyl)-ethyl]-butyronitrile 
• 24522-98-3 1,5-Bis-<3-benzolazo-phenyl>-pentan-3-on-azin 
• 162467-43-8 2,3,5,6-Tetrahydro-2,6-di(3-nitrophenyl)thiopyran-4-one 1,1-dioxide 

Relevant articles and documents

Significance of the analysis reaction of isopropanol with 3-nitrobenzaldehyde

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Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors

A series of dibenzylideneacetones (A1-A12) and some of their pyrazolines (B1-B4) were synthesized and evaluated in vitro for blood stage antiplasmodial properties in Plasmodium falciparum culture using SYBR-green-I fluorescence assay. The compound (1E, 4E)-1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (A9) was found to be the most active with IC50 of 1.97 μM against chloroquine-sensitive strain (3D7) and 1.69 μM against chloroquine-resistant field isolate (RKL9). The MTT based cytotoxicity assay on HeLa cell line has confirmed that A9 is selective in its action against malaria parasite (with a therapeutic index of 166). Our results revealed that these compounds exhibited promising antiplasmodial activities which can be further explored as potential leads for the development of cheaper, safe, effective and potent drugs against chloroquine-resistant malarial parasites.

Symmetrical α-bromoacryloylamido diaryldienone derivatives as a novel series of antiproliferative agents. Design, synthesis and biological evaluation

In a continuing study of hybrid compounds containing the α-bromoacryloyl moiety as potential anticancer drugs, we synthesized a novel series of hybrids 4a-h, in which this moiety was linked to a 1,5-diaryl-1,4-pentadien-3-one system. Many of the conjugates prepared (4b, 4c, 4e and 4g) demonstrated pronounced, submicromolar antiproliferative activity against four cancer cell lines. Moreover, compound 4b induced apoptosis through the mitochondrial pathway and activated caspase-3 in a concentration-dependent manner.