52168-41-9

Usage

Molecular weight

287.17 g/mol

Appearance

yellow solid
Commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds

Also known as

1-(4-Bromophenyl)-1-phenylpropan-1-one
Contains a phenyl ring with a bromine substituent at the 4-position and a propiophenone moiety
Used as a building block in organic synthesis
Utilized in the production of benzylamines, styrenes, and similar compounds

Upstream product

• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 10388-32-6 1-phenyl-3-(4-bromophenyl)-2,3-dibromo-1-propanone 
• 259099-03-1 3-(4-bromophenyl)-N-methoxy-N-methylpropanamide 
• 100-58-3 phenylmagnesium bromide 
• 98-85-1 1-Phenylethanol 
• 873-75-6 4-bromobenzenemethanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 49678-04-8 trans-4-bromocinnamaldehyde 
• 98-80-6 phenylboronic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 100-52-7 benzaldehyde 
• 96-09-3 styrene oxide 

Downstream Products

• 905590-36-5 2-amino-5-(4-bromobenzyl)-4-phenylthiophene-3-carboxylic acid ethyl ester 
• 1180676-68-9 ethyl 5-(4-bromophenyl)-3-phenylpent-2-enoate 
• 1180676-67-8 ethyl 5-(4-bromophenyl)-3-phenylpent-2-enoate 

Relevant academic research and scientific papers

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

Controlling Chemoselectivity of Catalytic Hydroboration with Light

The ability to selectively react one functional group in the presence of another underpins efficient reaction sequences. Despite many designer catalytic systems being reported for hydroboration reactions, which allow introduction of a functional handle fo

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.

Synthesis of α-Alkylated Ketones via Selective Epoxide Opening/Alkylation Reactions with Primary Alcohols

A new method for converting terminal epoxides and primary alcohols into α-alkylated ketones under borrowing hydrogen conditions is reported. The procedure involves a one-pot epoxide ring opening and alkylation via primary alcohols in the presence of an N-heterocyclic carbene iridium(I) catalyst, under aerobic conditions, with water as the side product.

Electrochemical-Induced Hydrogenation of Electron-Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor

Efficient hydrogenation of electron-deficient internal olefins and alkynes access to saturate ketone with CH3OH as a single hydrogen donor under electrochemical conditions has been successfully developed. This hydrogenation strategy can be used to convert electron-deficient internal olefins and alkynes to saturate ketone under electrochemical conditions with exogenous-reductant and a metal catalyst. Mechanistic studies reveal that radical hydrogenation was involved in this transformation. Notably, various electron-deficient internal olefins and alkynes could be tolerated in such an electrochemical hydrogenation synthetic strategy and can be easily scaled up with good efficiency. (Figure presented.).

Neutral-eosin Y-catalyzed regioselective hydroacylation of aryl alkenes under visible-light irradiation

Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity by using neutral eosin Y as a direct hydrogen-atom-transfer (HAT) catalyst under visible-light irradiation. Aldehydes and styrenes with various substituents were tolerated (>20 examples), giving the corresponding products in moderate to high yields. The key acyl radical intermediate was generated from a direct HAT process induced by photoexcited eosin Y. Subsequent addition to styrenes and a reverse HAT process generated the ketone products.

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Method for synthesizing alpha-alkylated ketone in water

The invention discloses a method for synthesizing alpha-alkylated ketone in water. The method comprises the following steps: adding ketone, compound alcohol, a transition metal iridium catalyst, an alkali and a solvent, namely water into a reaction container, carrying out a reflux reaction on a reaction mixture in the air for several hours, carrying out cooling to room temperature, carrying out rotary evaporation to remove the solvent, and carrying out column separation (ethyl acetate/petroleum ether) to obtain a target compound, namely alpha-alkylated ketone. A reaction equivalent substrate is used in the reaction process, so raw material waste is avoided; equivalent alkali is used, so better environmental protection performance is obtained; water reflux reaction conditions are milder; and non-toxic and harmless pure water is used as the solvent in the reaction, only water is generated as a by-product, so atom reaction economy is high, and the requirements of green chemistry are met.

Synthesis and catalytic applications of Ru and Ir complexes containing N,O-chelating ligand

A series of monometallic complexes (Ru1–3, Ir1–3) which have N,O-chelating ligand (pyrazine-2-carboxylate (1), pyridine-2-carboxylate (2), quinoline carboxylate(3) and bimetallic complexes (Ru4,5, Ir4,5) bridged by pyrazine-2,3- dicarboxylate (4) and imidazole-4,5-dicarboxylate(5) were synthesized and characterized by 1H-, 13C NMR, FT-IR, and elemental analysis. The crystal structure of Ir2 was determined by X-ray crystallography. The complexes (Ru1–5, Ir1–5) were applied to investigate the electronic and steric effect of ligand in their catalytic activities in transfer hydrogenation and alpha(α)-alkylation reaction of ketones with alcohols. The activities of iridium complexes (Ir1–5) were much more efficient than ruthenium complexes (Ru1–5). The highest activity for both reactions was observed for the complex (Ir2) with pyridine-2-carboxylate. The Ir hydride species was monitored for both reactions.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.