22966-26-3

Basic information

• Product Name: 1-(3-bromophenyl)-3-phenylprop-2-en-1-one
• CAS NO: 22966-26-3
• Molecular Formula: C₁₅H₁₁BrO
• Molecular Weight: 287.1512
• Mol File: 22966-26-3.mol

Chemical Properties

• Boiling Point: 403.4°C at 760 mmHg
• Flash Point: 83.2°C
• Density: 1.393g/cm³
• Vapor Pressure: 1.02E-06mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 1-(3-bromophenyl)-3-phenylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-bromophenyl)-3-phenylprop-2-en-1-one(22966-26-3)
• EPA Substance Registry System: 1-(3-bromophenyl)-3-phenylprop-2-en-1-one(22966-26-3)

Safety Data

• Hazardous Substances Data: 22966-26-3(Hazardous Substances Data)

Usage

Appearance

Yellow solid

Usage

Commonly used in organic synthesis and pharmaceutical research

Chemical structure

Ketone derivative containing a bromophenyl group and a phenylpropenone group

Applications

a. Reactant in the synthesis of various biologically active compounds
b. Potential anti-inflammatory properties
c. Potential antitumor properties
d. Development of new synthetic methodologies
e. Preparation of complex molecules for medicinal purposes

Upstream product

• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 100-51-6 benzyl alcohol 
• 52780-14-0 1-(3-bromophenyl)ethanol 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 66107-31-1 3-bromophenyl trifluoromethanesulfonate 
• 278168-68-6 1-(3-bromophenyl)-3-phenylprop-2-yn-1-ol 
• 3132-99-8 m-bromobenzoic aldehyde 
• 536-74-3 phenylacetylene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 7194-78-7 (3-bromophenyl)oxoacetic acid 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 

Downstream Products

• 105065-87-0 rac-(E)-1-(3-bromophenyl)-3-phenylprop-2-en-1-ol 
• 105065-88-1 1-Bromo-3-((E)-1-bromo-3-phenyl-allyl)-benzene 
• 105065-96-1 (9E,13E)-11,12-Diphenyl-tricyclo[13.3.1.1^4,8]icosa-1⁽¹⁸⁾,4⁽²⁰⁾,5,7,9,13,15⁽¹⁹⁾,16-octaene 
• 105065-90-5 C₃₂H₂₆O₂ 
• 105065-89-2 C₃₀H₂₄Br₂ 
• 105065-94-9 (10E,14E)-12,13-Diphenyl-3-thia-tricyclo[14.3.1.1^5,9]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,8,10,14,16⁽²⁰⁾,17-octaene 
• 105065-91-6 {3-[(E)-2-(3-Hydroxymethyl-phenyl)-4-phenyl-1-((E)-styryl)-but-3-enyl]-phenyl}-methanol 
• 105065-92-7 C₃₂H₂₈Br₂ 
• 539857-07-3 C₂₁H₁₉BrO₃ 
• 133131-50-7 4-(3-bromo-phenyl)-4-oxo-2-phenyl-butyronitrile 
• 1148058-80-3 4-[3'-bromophenyl]-6,7-dimethyl-2-phenyl-2,3-dihydro-1,5-benzothiazepine 

Relevant articles and documents

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions

High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.

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.

Regioselective α-Deuteration of Michael Acceptors Mediated by Isopropylamine in D2O/AcOD

Site-specific hydrogen/deuterium exchange is an important method to access deuterated compounds for chemical and biological studies. Herein is reported the first method for the regioselective α-deuteration of enals and enones. The transformation features D2O and AcOD as deuterium sources and amines as organocatalysts. The deuteration strategy is scalable and works on enals with a variety of substituted arene or heterocycle motifs as well as enones. The method has been applied to the synthesis of deuterated drug precursors.

Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.

Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices

A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.

Pyrazolopyrimidine compound and application thereof as well as luminescent device

The invention provides a pyrazolopyrimidine compound; the structural formula of the pyrazolopyrimidine compound is shown in the description. The pyrazolopyrimidine compound has better thermal stability, high luminous efficiency and high luminescence purit

A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water

A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.

Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes

Although hydroacylation is a very useful reaction for producing ketones from aldehydes with 100% atom efficiency, classical Rh-catalyzed hydroacylation presents several problems, including the need for transition metal catalysts, unwanted decarbonylation of aldehydes, and difficulty in regioselectivity control. However, formal hydroacylation utilizing the nucleophilicity of terminal alkynes can avoid these problems. In this work, we have achieved transition-metal-free formal hydroacylation of terminal alkynes using an Mg3Al-CO3-layered double hydroxide as a heterogeneous catalyst. This system was applicable to the efficient synthesis of α,β-unsaturated ketones with various substituents, and the catalyst can be reused without a significant loss of catalytic performance.

Synthesis and antitrypanosomal activities of novel pyridylchalcones

A library of novel pyridylchalcones were synthesised and screened against Trypanosoma brucei rhodesiense. Eight were shown to have good activity with the most potent 8 having an IC50value of 0.29?μM. Cytotoxicity testing with human KB cells showed a good selectivity profile for this compound with a selectivity index of 47. Little activity was seen when the library was tested against Leishmania donovani. In conclusion, pyridylchalcones are promising leads in the development of novel compounds for the treatment of human African trypanosomiasis (HAT).