22966-09-2

Basic information

• Product Name: (E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one
• Synonyms: (E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one;(E)-β-(4-Bromophenyl)acrylophenone;(E)-3-(4-BROMOPHENYL)-1-PHENYLPROP-2-EN-1-ONE
• CAS NO: 22966-09-2
• Molecular Formula: C₁₅H₁₁BrO
• Molecular Weight: 287.1512
• Mol File: 22966-09-2.mol

Chemical Properties

• Boiling Point: 398.3°Cat760mmHg
• Flash Point: 79.6°C
• Appearance: /
• Density: 1.393g/cm³
• Vapor Pressure: 1.49E-06mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: (E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one(22966-09-2)
• EPA Substance Registry System: (E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one(22966-09-2)

Safety Data

• Hazardous Substances Data: 22966-09-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one is used as a pharmaceutical compound for its potential antioxidant, anti-inflammatory, and anticancer activities. It has been studied for its ability to modulate various signaling pathways and exert inhibitory effects on tumor growth and progression.
Used in Food Industry:
(E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one is used as a food preservative and dye due to its potential applications in extending the shelf life of food products and providing color.
Used in Materials Science:
(E)-1-Phenyl-3-(4-bromophenyl)-2-propene-1-one is used in materials science for its potential applications in the synthesis of various other organic compounds and its versatility in different fields.

InChI:InChI=1/C15H11BrO/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11H/b11-8+

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 98-86-2 acetophenone 
• 111873-49-5 Te-phenacyldi(n-butyl)telluronium bromide 
• 70-11-1 α-bromoacetophenone 
• 73654-15-6 (Z)-3-(4-Bromo-phenyl)-1-phenyl-propenone 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 10388-32-6 1-phenyl-3-(4-bromophenyl)-2,3-dibromo-1-propanone 
• 96-09-3 styrene oxide 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 536-74-3 phenylacetylene 
• 135885-91-5 3-Benzoyl-2,6-bis-(4-bromo-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester 
• 1200-07-3 trans-4-bromocinnamic acid 
• 71-43-2 benzene 
• 57-13-6 urea 

Downstream Products

• 89451-26-3 4-(4-Bromo-phenyl)-6-hydroxy-6-phenyl-2-thioxo-piperidine-3-carbonitrile; compound with piperidine 
• 101855-03-2 3-(4-bromo-phenyl)-3-methoxyamino-1-phenyl-propan-1-one 
• 1027245-31-3 4-[1-(4-Bromo-phenyl)-3-oxo-3-phenyl-propyl]-3,4-dihydro-1H-benzo[b]azepine-2,5-dione 
• 606-86-0 1,3,3-triphenylpropan-1-one 
• 330961-77-8 (2R,3R)-3-(4-Bromo-phenyl)-2-methyl-1,5-diphenyl-pentane-1,5-dione 
• 77472-76-5 (3-(4-bromophenyl)aziridin-2-yl)(phenyl)methanone 
• 5472-01-5 3-(4-bromophenyl)-1,3-diphenylpropan-1-one 
• 219607-51-9 3-(4-bromophenyl)-4-nitro-1-phenylbutan-1-one 

Relevant articles and documents

Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization

Katritzky salts have emerged as effective alkyl radical sources upon metal- or photocatalysis. These are typically prepared from the corresponding triarylpyrylium ions, in turn an important class of photocatalysts for small molecules synthesis and photopolymerization. Here, a flow method for the rapid synthesis of both pyrylium and Katrizky salts in a telescoped fashion is reported. Moreover, several pyrylium salts were tested in the photoinduced RAFT polymerization of vinyl ethers under flow and batch conditions.

Synthesis, crystal structure, Hirshfeld surface analysis and DNA binding studies of 1-((E)-3-(4-bromophenyl)-1-phenylallylidene)-2-(m-tolyl)hydrazine

1-((E)-3-(4-bromophenyl) -1-phenylallylidene)-2-(m-tolyl)hydrazine (4) was synthesized and characterized for structural elucidation by spectroscopy (FT-IR, 1H NMR, and 13C NMR) and single crystal X-ray diffraction. In the title compo

Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones

Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).

Deep blue fluorescent material with a narrow FWHM based on indolo[3,2,1-jk]carbazol/pyrimidine hybrids

A series of blue fluorescent materials containing electron accepting pyrimidine and electron donating bis(biphenyl)amine, diphenylcarbazole, and diphenylindolo[3,2,1-jk]carbazole moieties were synthesized in moderate yields, and their optical and electroc

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.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range

Abstract: To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones (15–36 and 37–41) and structurally related compounds (42–47) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10?μM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (Ki (r) = 1.6?μM). The structure–affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38—that contains an α,?-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract: C3 amino-substituted chalcone derivative (38) with C3′ Br substitution on benzylidene ring B possesses selective adenosine rA1 receptor affinity in micromolar range.[Figure not available: see fulltext.]

Reaction rate differences between organotrifluoroborates and boronic acids in BINOL-catalyzed conjugate addition to enones

Enantioselective organocatalysis has been successfully employed in combination with trifluoroborate reagents for novel organic transformations over the last decade. However, no experimental rate studies of these reactions have been reported. Herein we report Hammett plot analysis of the organocatalyzed enantioselective conjugate addition of alkenyl, aryl, and heteroaryl trifluoroborate salts to chalcone derivatives with substitution at both the β-aryl and keto-aryl positions. The rate trend for keto-aryl substitution diverges from that of boronic acid nucleophiles in that the keto-aryl substituent for trifluoroborate salts does not measurably impact reaction rate in a manner consistent with charge stabilization. In addition, variable temperature NMR in combination with quantitative thin-layer chromatography (TLC) analysis suggests that the reaction is impacted by the low solubility of the trifluoroborate salts, so particle size and stirring speed affect reaction rates.

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration

The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.