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 
• 131401-44-0 2-Benzenesulfonyl-3-(4-bromo-phenyl)-1-phenyl-propan-1-one 
• 123558-68-9 α-(p-bromobenzylidene)-β-keto sulfone 
• 123558-72-5 α-(p-bromobenzyl)-β-keto sulfone 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 5467-74-3 4-Bromophenylboronic acid 
• 768-03-6 Phenyl vinyl ketone 
• 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 
• 22966-09-2 (2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 98-85-1 1-Phenylethanol 
• 873-75-6 4-bromobenzenemethanol 

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

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

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.

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.

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.

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.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

C-C coupling formation using nitron complexes

A series of RuII (1), RhIII (2), IrIII (3, 4), IrI (5) and PdII (6-9) complexes of the 'instant carbene' nitron were prepared and characterized by 1H- and 13C-NMR, FT-IR and elemental analysis. The molecular structures of complexes 1-4 and 6 were determined by X-ray diffraction studies. The catalytic activity of the complexes (1-9) was evaluated in alpha(α)-alkylation reactions of ketones with alcohol via the borrowing hydrogen strategy under mild conditions. These complexes were able to perform this catalytic transformation in a short time with low catalyst and base amounts under an air atmosphere. Also, the PdII-nitron complexes (6-9) were applied in the Suzuki-Miyaura C-C coupling reaction and these complexes successfully initiated this reaction in a short time (30 minutes) using the H2O/2-propanol (1.5?:?0.5) solvent system. The DFT calculations revealed that the Pd0/II/0 pathway was more preferable for the mechanism