102477-83-8

Basic information

• Product Name: biphenyl-4-propiophenone
• Synonyms: biphenyl-4-propiophenone;1-(4-biphenylphenyl)propan-1-one
• CAS NO: 102477-83-8
• Molecular Formula: C₂₁H₁₈O
• Molecular Weight: 286.36702
• Mol File: 102477-83-8.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: biphenyl-4-propiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: biphenyl-4-propiophenone(102477-83-8)
• EPA Substance Registry System: biphenyl-4-propiophenone(102477-83-8)

Safety Data

• Hazardous Substances Data: 102477-83-8(Hazardous Substances Data)

Usage

General Description

Biphenyl-4-propiophenone, also known as 4'-biphenyl-4-ylpropiophenone, is a chemical compound with the molecular formula C15H12O. It is a bright yellow solid with a melting point of 69-73 degrees Celsius. biphenyl-4-propiophenone is commonly used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes. Biphenyl-4-propiophenone is also utilized as a reagent in organic chemistry reactions, such as the formation of carbon-carbon and carbon-oxygen bonds. Additionally, it has applications in the production of fragrances and flavors due to its aromatic properties.

Upstream product

• 98-85-1 1-Phenylethanol 
• 712-76-5 N-(4-phenyl)benzylamine 
• 98-86-2 acetophenone 
• 2350-89-2 p-vinylbiphenyl 
• 100-52-7 benzaldehyde 
• 1074-12-0 phenylglyoxal hydrate 
• 3218-36-8 4-Phenylbenzaldehyde 
• 3597-91-9 biphenyl-4-yl methanol 
• 36047-01-5 3-(biphenyl-4-yl)-1-phenylprop-2-en-1-one 

Downstream Products

• 1180676-80-5 ethyl 5-(biphenyl-4-yl)-3-phenylpent-2-enoate 
• 1180676-79-2 ethyl 5-(biphenyl-4-yl)-3-phenylpent-2-enoate 
• 2350-89-2 p-vinylbiphenyl 

Relevant articles and documents

RuHCl(CO)(PPh3)3-catalyzed R-alkylation of ketones with primary alcohols

The α-alkylation reaction of ketones with primary alcohols to give α-alkylated ketones was achieved using RuHCl(CO)(PPh3) 3 as a catalyst in the presence of Cs2CO3 as a base. This reaction proceeds via an aldol condensation of ketones with aldehydes, formed via transfer dehydrogenation of alcohols, to give α,β-unsaturated ketones, which then undergo transfer hydrogenation with primary alcohols to give R-alkylated ketones and aldehydes, the latter of which participate in the next catalytic cycle. While the reaction of aliphatic primary alcohols was sluggish compared with that of benzylic alcohols, a catalytic amount of 1,10-phenanthroline was found to promote the alkylation dramatically.

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.

Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled Ruthenium-Catalyzed Deaminative α-Alkylation of Ketones with Amines

The catalytic system formed in situ from the reaction of a cationic Ru-H complex with 3,4,5,6-tetrachloro-1,2-benzoquinone was found to mediate a regioselective deaminative coupling reaction of ketones with amines to form the α-alkylated ketone products. Both benzylic and aliphatic primary amines were found to be suitable substrates for the coupling reaction with ketones in forming the α-alkylated ketone products. The coupling reaction of PhCOCD3 with 4-methoxybenzylamine showed an extensive H/D exchange on both α-CH2 (41% D) and β-CH2 (21%) positions on the alkylation product. The Hammett plot obtained from the reaction of acetophenone with para-substituted benzylamines p-X-C6H4CH2NH2 (X = OMe, Me, H, F, Cl, CF3) showed a strong promotional effect by the amine substrates with electron-releasing groups (ρ = -0.49 ± 0.1). The most significant carbon isotope effect was observed on the α-carbon of the alkylation product (Cα = 1.020) from the coupling reaction of acetophenone with 4-methoxybenzylamine. The kinetics of the alkylation reaction from an isolated imine substrate led to the empirical rate law: rate = k[Ru][imine]. A catalytically active Ru-catecholate complex was synthesized from the reaction of the cationic Ru-H complex with 3,5-di-tert-butyl-1,2-benzoquinone and PCy3. The DFT computational study was performed on the alkylation reaction, which revealed a stepwise mechanism of the [1,3]-carbon migration step via the formation of a Ru(IV)-alkyl species with a moderate energy of activation (ΔG? = 32-42 kcal/mol). A plausible mechanism of the catalytic alkylation reaction via an intramolecular [1,3]-alkyl migration of an Ru-enamine intermediate has been compiled on the basis of these experimental and computational data.