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.

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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.

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights

Fifteen chalcone derivatives having D–A–D, D–A–A and A–A–D architectures have been synthesized by Claisen–Schmidt condensation reaction and characterized by UV–Vis, IR, 1H-NMR, 13C-NMR and Mass spectrometry. In order to unambiguously establish the structure–activity relationship for the non-linear optical activity of these compounds, for the first time to our knowledge, we use the femtosecond degenerate four wave mixing (DFWM) technique to quantify and compare the third-order non-linear optical (NLO) activity of all the 15 compounds, under identical conditions. The second harmonics generation (SHG) efficiencies for all the compounds have also been evaluated using the Kurtz-Perry powder method. Among the compounds that we have synthesized here, the ones with A–A–D architecture show the highest NLO activity. Our results show that the NLO activity of a compound with A–A–D architecture can be further enhanced by incorporating a substituent with strong electron withdrawing ability on ring A and strong electron donating substituent on ring B. The results of the in silico studies that we have carried out correlate well with our experimental findings. The compounds (E)-3-(4-(dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-N(CH3)2–4′-NO2) and (E)-3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-MeO-4′-NO2) show the highest NLO activity among the compounds we have reported here. Graphical abstract: [Figure not available: see fulltext.]