22966-23-0

Basic information

• Product Name: (E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one
• Synonyms: (2E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one;(E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one;(E)-3-Phenyl-1-(4-bromophenyl)-2-propene-1-one;(E)-4'-Bromochalcone;(E)-1-(4-Bromophenyl)-3-phenyl-2-propen-1-one;2-Propen-1-one, 1-(4-bromophenyl)-3-phenyl-, (E)-;trans-4'-Bromochalcone
• CAS NO: 22966-23-0
• Molecular Formula: C₁₅H₁₁BrO
• Molecular Weight: 287.15
• Mol File: 22966-23-0.mol

Chemical Properties

• Boiling Point: 402.2°C at 760 mmHg
• Flash Point: 82.4°C
• Appearance: /
• Density: 1.393g/cm³
• Vapor Pressure: 1.12E-06mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: (E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one(22966-23-0)
• EPA Substance Registry System: (E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one(22966-23-0)

Safety Data

• Hazardous Substances Data: 22966-23-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one is used as an intermediate in the synthesis of various pharmaceuticals for its ability to be a building block in the creation of different medicinal compounds.
Used in Fragrance and Flavor Industry:
(E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one is used as a scent in perfumes and cosmetics for its distinctive odor, contributing to the creation of various fragrances and flavors.
Used in Organic Synthesis:
(E)-1-(4-Bromophenyl)-3-phenyl-2-propene-1-one is used as a valuable building block in the chemical industry for the synthesis of a wide range of organic compounds, showcasing its versatility and importance in chemical research and development.

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

Upstream product

• 99-90-1 para-bromoacetophenone 
• 100-52-7 benzaldehyde 
• 201230-82-2 carbon monoxide 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 99-73-0 para-bromophenacyl bromide 
• 589-87-7 1,4-bromoiodobenzene 
• 536-74-3 phenylacetylene 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 102752-32-9 diethyl 2-(3-(4-bromophenyl)-3-oxo-1-phenylpropyl)malonate 
• 72997-91-2 4-(4-bromo-phenyl)-(trans-3-phenyl-aziridin-2-yl)-ketone 
• 1122-91-4 4-bromo-benzaldehyde 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 

Downstream Products

• 101854-96-0 1-(4-bromo-phenyl)-3-methoxyamino-3-phenyl-propan-1-one 
• 132060-23-2 C₁₉H₂₁BrN₂O₂S 
• 86118-56-1 cis,trans-2,3-Diphenyl-1-(p-bromobenzoyl)cyclopropane 
• 603-35-0 triphenylphosphine 
• 107710-46-3 Dithiocarbamic acid 3-(4-bromo-phenyl)-3-oxo-1-phenyl-propyl ester 
• 29425-81-8 (4-bromophenyl)(3-phenyloxiran-2-yl)methanone 
• 1669-51-8 1‐(4‐bromophenyl)‐3‐phenylpropan‐1‐one 
• 32157-71-4 trans-1-(p-bromophenyl)-3-phenyl-2,3-epoxy-1-propanone 
• 111505-40-9 1,6-Bis-(4-bromo-phenyl)-3,4-diphenyl-hexane-1,6-dione 
• 87116-44-7 [5-(4-Bromo-benzoyl)-2,4-diphenyl-tetrahydro-thiophen-3-yl]-(4-bromo-phenyl)-methanone 
• 132042-55-8 C₂₅H₂₆BrN₃O₂S 
• 64820-47-9 4-(4-bromophenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine 
• 135701-17-6 C₂₃H₂₇BrN₂O₂S 
• 134045-71-9 5-(4-Bromo-phenyl)-7-phenyl-3-p-tolylazo-pyrazolo[1,5-a]pyrimidin-2-ylamine 

Relevant articles and documents

Synthesis of a new 1,2,3,4,5-pentasubstituted cyclohexanol and determining its stereochemistry by NMR spectroscopy and quantum-chemical calculations

The presence of substituents in cyclohexane can influence to the ratio of conformers; for some cases, the boat form is preferable. The new six-membered cyclohexanol derivative 2 has been obtained by the synthesis of (E)-1-(bromophenyl)-3-phenylpropen-2-one (1). The NMR and quantum-chemical conformational analysis for the 2 have carried out, and its possible mechanism of formation was given.

Pyridoimidazole derivatives as well as preparation method and application thereof

The invention discloses pyridoimidazole derivatives as well as a preparation method and application thereof. The pyridoimidazole derivatives with two D-pi-A structures are synthesized on the basis that pyridoimidazole serves as an electron acceptor system by means of the electron donating property of phenanthroimidazole/diphenylamine. The pyridoimidazole derivatives can serve as photoinitiators, and the two photoinitiators both have longer conjugated chain lengths, so that the photon absorption cross section is increased, the photoinitiators can initiate polymerization reaction at the wavelength of 365 nm, have higher polymerization efficiency, and can be widely applied to the field of ultraviolet curing.

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.

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.

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.]

Synthesis and antimicrobial evaluation of arylated 1,3,5-triphenyl pyrazoline derivatives using suzuki-miyaura reactions

The first palladium –catalyzed coupling reactions of 1,3,5-triphenyl pyrazoline are reported. The Suzuki-Miyaura reaction of 3-(4-bromophenyl)-1,5-diphenyl pyrazoline with one equivalent of arylboronic acids afforded 3-(biphenyl)-1,5-diphenyl pyrazoline in 53-78 % yield. While the Suzuki-Miyaura reactions of 3,5-bis(4-bromophenyl)-1-phenyl pyrazoline with two equivalent of arylboronic acids gave 3,5-bis(biphenyl)-1-phenyl pyrazoline in 55-80% yield. The characterization of the synthesized derivatives (5a-h) and (6a-h) were accomplished on the basis of NMR, FT-IR, and mass techniques. The newly pyrazoline derivatives have been investigated for their in vitro antibacterial activity against gram- negative and gram-positive bacteria. The di-coupling compounds (6a-h) exhibited promising antibacterial against all four bacterial strains compared to the mono-coupling compounds (5a-h) which displayed a slight activity. The compound 6d showed a potent activity significantly more active than Trimethoprim (100μg/ml).

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.

Biological activity of novel pentasubstituted cyclohexanol against some microorganisms

The aim of this study is to investigate the antibacterial, antifungal activity of the new six membered 4-(4-bromophenyl)-4-hydroxy-2.6-diphenylcyclohexane-1.3-diyl)bis(4-bromophenyl)methanone and known (E)-1-(4-bromophenyl)-3phenylprop-2-en-1-one. The investigated products exhibit promising activities.

Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition

Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore, plausible mechanisms for the synthesis of different products have been proposed.

Green method for high-selectivity synthesis of chalcone compounds

Under the condition of air, the water-soluble inorganic weak base is used as a catalyst to catalyze the hydrogen transfer reaction of the propargyl alcohol compound, so that the green synthesis of the high-trans selective chalcone compound is realized. Reaction temperature: 80 - 120 °C and reaction time 12 - 48 hours. To the technical scheme, any transition metal catalyst and ligand do not need to be used, inert gas protection is not needed, no other byproducts are generated, the atom economy 100%, green and environment friendliness are avoided, and the product is a high-selectivity (E)-type product. The reaction conditions are relatively low in requirement. Compared with the prior art, the alkali catalyst is obvious in advantages, and has a certain application prospect in the fields of organic synthesis, biochemistry, medicine and the like.