1017-24-9

Basic information

• Product Name: 2-Phenyl-1-pyiridin-4-yl-ethanone
• Synonyms: 2-Phenyl-1-pyiridin-4-yl-ethanone;Ethanone, 2-phenyl-1-(4-pyridinyl)-;2-Phenyl-1-(4-pyridinyl)-ethanone;2-PHENYL-1-(PYRIDIN-4-YL)ETHAN-1-ONE
• CAS NO: 1017-24-9
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23254
• Mol File: 1017-24-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 346.4±17.0 °C(Predicted)
• Appearance: /
• Density: 1.127±0.06 g/cm3(Predicted)
• PKA: 3.11±0.10(Predicted)
• CAS DataBase Reference: 2-Phenyl-1-pyiridin-4-yl-ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-1-pyiridin-4-yl-ethanone(1017-24-9)
• EPA Substance Registry System: 2-Phenyl-1-pyiridin-4-yl-ethanone(1017-24-9)

Safety Data

• Hazardous Substances Data: 1017-24-9(Hazardous Substances Data)

Usage

General Description

2-Phenyl-1-pyridin-4-yl-ethanone, also known as 4-Acetylphenylpyridine, is a chemical compound with the molecular formula C13H11NO. It is a ketone derivative with a pyridine ring and a phenyl group attached to it. 2-Phenyl-1-pyiridin-4-yl-ethanone is used in the pharmaceutical industry as a building block for the synthesis of various drugs and pharmaceuticals. It also has potential applications in organic synthesis and medicinal chemistry due to its unique structure and reactivity. Additionally, it has been studied for its potential biological activities, including its ability to exhibit antimicrobial and anti-inflammatory properties. Overall, 2-Phenyl-1-pyridin-4-yl-ethanone has diverse potential applications and properties that make it a valuable compound in various fields.

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 908094-04-2 phenyldiazomethane 
• 100-48-1 pyridine-4-carbonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 100240-06-0 4-(phenylacetyl)pyridinium chloride 
• 114443-74-2 4-(phenylacetyl)pyridinium bromide 
• 114443-84-4 1-(phenylamino)-1-(4-pyridyl)-2-phenylethylene 
• 3360-72-3 (anilino-pyridin-4-yl-methyl)-phosphonic acid diphenyl ester 
• 1570-45-2 isonicotinic acid ethylester 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 
• 27768-46-3 N-(pyridin-4-ylmethylene)aniline 
• 100-44-7 benzyl chloride 
• 140-29-4 phenylacetonitrile 
• 1692-15-5 4-pyridylboronic acid 

Downstream Products

• 114443-53-7 1-Methyl-4-phenylacetyl-pyridinium; bromide 
• 135303-13-8 1-Benzyl-4-phenylacetyl-pyridinium; bromide 
• 134242-09-4 2-phenyl-1-(pyridine-4-yl)butan-1-one 
• 137537-16-7 3-Hydroxy-4-phenyl-3-(4-pyridyl)butansaeuremethylester 
• 135303-14-9 1-(4-Bromo-benzyl)-4-phenylacetyl-pyridinium; bromide 
• 135303-15-0 1-(3-Chloro-benzyl)-4-phenylacetyl-pyridinium; bromide 
• 135303-17-2 1-(4-Cyano-benzyl)-4-phenylacetyl-pyridinium; bromide 
• 135303-16-1 1-(3-Cyano-benzyl)-4-phenylacetyl-pyridinium; bromide 
• 135303-18-3 1-(3-Nitro-benzyl)-4-phenylacetyl-pyridinium; bromide 
• 135303-19-4 1-(4-Nitro-benzyl)-4-phenylacetyl-pyridinium; bromide 
• 101986-12-3 2-brom-2-phenyl-1-(4-pyridyl)-1-ethanon hydrobromid 
• 1283117-85-0 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(pyridin-4-yl)-3,4-dihydropyrimidin-2(1H)-one 
• 1352037-95-6 3-phenyl-2-(pyridin-4-yl)-1,7-naphthyridine 
• 59576-23-7 2-phenyl-1-(pyridin-4-yl)ethylamine 

Relevant articles and documents

Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones

A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.

Intramolecular cation-π interactions control the conformation of nonrestricted (phenylalkyl)pyridines

NOEsy and fluorescence spectroscopy reveal that conversion of conformationally flexible (phenylalkyl)pyridines into their corresponding N-methyl-pyridinium iodides results in intramolecular π-stacking. The Royal Society of Chemistry.

Proton activating factors and keto-enol-zwitterion tautomerism of 2-, 3- And 4-phenylacetylpyridines

Equilibrium constants for keto-enol tautomerism of 2-, 3- and 4-phenylacetylpyridines in aqueous solution at 25°C have been measured as pKTE = 3.35, 4.2 and 3.1 respectively (KTE = [enol]/[ketone], PKTE = -log KTE). Corresponding values for the N-protonated ketones are 1.64, 2.80 and 1.54. These enol contents are consistently higher than those of the isomeric phenacylpyridines, except in the case of the (unprotonated) 2-isomer where the greater enol content of the latter (pKTE = 2.0) can be attributed to more effective stabilization by hydrogen-bonding to the pyridyl nitrogen in a six- than five-membered ring. The tautomeric constants were obtained by combining rate constants for enolisation, measured by halogen trapping, with rate constants for relaxation of the enol tautomer (generated by quenching the enolate anion into acid or acidic buffers) to its more stable keto isomer. Approximate tautomeric constants for zwitterion formation (pKTZ = 4.6, 7.4 and 6.1 for 2-, 3- and 4-isomers respectively) are inferred from measurements of ionisation constants and keto-enol tautomeric constants for N-methylated ketones by taking the N-methylated enolate anions as models for the zwitterions and correcting for the substituent effect of the methyl group. The tautomerism is discussed in terms of the relationship pKT = ΔpKab + log PAF which dissects tautomeric constants into contributions from (a) a difference in pKas of non-interacting acidic and basic tautomeric sites (ΔpKab) and (b) a mutual stabilisation of these sites from conjugative, inductive or hydrogen-bonded interactions between them. This stabilisation is described by a proton activating factor (PAF) measuring the effect of protonation at one tautomeric site upon the ionisation constant at the other.