20432-02-4

Basic information

• Product Name: (2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one
• Synonyms: (2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one;(E)-1-(4-Nitrophenyl)-3-phenyl-2-propen-1-one;2-Propen-1-one, 1-(4-nitrophenyl)-3-phenyl-, (E)- (9ci);Chalcone, 4'-nitro-, (E)-;(2E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-one
• CAS NO: 20432-02-4
• Molecular Formula: C₁₅H₁₁NO₃
• Molecular Weight: 253.2527
• Mol File: 20432-02-4.mol
• Article Data: 115

Chemical Properties

• Boiling Point: 441°Cat760mmHg
• Flash Point: 214.9°C
• Appearance: /
• Density: 1.255g/cm³
• CAS DataBase Reference: (2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one(20432-02-4)
• EPA Substance Registry System: (2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one(20432-02-4)

Safety Data

• Hazardous Substances Data: 20432-02-4(Hazardous Substances Data)

Usage

General Description

(2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one, also known as p-nitrochalcone, is a chemical compound with the formula C15H11NO3. It is a bright yellow solid that is insoluble in water but soluble in organic solvents. It is often used as a precursor in the synthesis of other chemical compounds such as flavonoids and dyes. P-nitrochalcone has also been studied for its potential medicinal properties, including its ability to inhibit the growth of certain cancer cells and its anti-inflammatory effects. Its structure consists of a chalcone backbone with a nitro group attached to the phenyl ring, making it a versatile building block for various chemical reactions and applications.

Upstream product

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Downstream Products

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• 111336-88-0 3-Methyl-5-(4-nitro-phenyl)-1,7-diphenyl-1,6,7,8-tetrahydro-pyrazolo[3,4-b][1,4]diazepine 
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• 54914-77-1 1-(4-nitrophenyl)-3-phenyl-1-propanone 
• 122-78-1 phenylacetaldehyde 
• 62-23-7 4-nitro-benzoic acid 
• 40327-57-9 trans-2,3-epoxy-1-(4-nitrophenyl)-3-phenylpropan-1-one 

Relevant articles and documents

Synthesis and anti-inflammatory activity of three nitro chalcones

The aim of this study was to synthesize three nitro substituted chalcones and to evaluate their anti-inflammatory activity in the model of carrageenan induced edema in rats. The nitro chalcone were prepared by aldol condensation using of mechanical agitation and environmentally friendly solvents with 72-73% yields in approximately 2 h. The three structures were evaluated on biological activity at dose of 200 mg/kg and they showed anti-inflammatory protective effect by both oral and intraperitoneal administration, this effect was time dependent.

Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B

A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.

Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC

A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.