17123-83-0

Basic information

• Product Name: 1-(morpholin-4-yl)-2-phenylethanone
• Synonyms: 1-morpholino-2-phenylethan-1-one; ethanone, 1-(4-morpholinyl)-2-phenyl-; Morpholine, 4-(phenylacetyl)-
• CAS NO: 17123-83-0
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 17123-83-0.mol
• Article Data: 70

Chemical Properties

• Boiling Point: 382.9°C at 760 mmHg
• Flash Point: 185.4°C
• Density: 1.137g/cm³
• Vapor Pressure: 4.56E-06mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: 1-(morpholin-4-yl)-2-phenylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(morpholin-4-yl)-2-phenylethanone(17123-83-0)
• EPA Substance Registry System: 1-(morpholin-4-yl)-2-phenylethanone(17123-83-0)

Safety Data

• Hazardous Substances Data: 17123-83-0(Hazardous Substances Data)

Usage

General Description

1-(morpholin-4-yl)-2-phenylethanone, also known as para-morpholinopropiophenone, is a chemical compound with the molecular formula C13H17NO2. It is a ketone derivative that contains a morpholine group and a phenyl group. 1-(morpholin-4-yl)-2-phenylethanone is often used in the synthesis of pharmaceuticals and other organic compounds. It has been identified as a key intermediate in the preparation of various drugs, including analgesics and psychotropic agents. It is also used as a reagent in the production of other organic compounds and is known for its diverse range of applications in chemical synthesis. Additionally, it is important to handle this chemical with care, as it has the potential to cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 110-91-8 morpholine 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 1696-20-4 4-acetylmorpholine 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 949-01-9 1-(morpholin-4-yl)-2-phenylethanethione 
• 38426-49-2 1-(morpholino)-2-phenylacetylene 
• 15159-40-7 4-morpholinocarbonyl chloride 
• 6921-34-2 benzylmagnesium chloride 
• 60-12-8 2-phenylethanol 
• 201230-82-2 carbon monoxide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 

Downstream Products

• 93999-62-3 4-(4-diethylamino-2-phenyl-butyryl)-morpholine 
• 93649-26-4 4-(phenyl-pyridin-2-yl-acetyl)-morpholine 
• 100232-79-9 4-[3-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-2-phenyl-propionyl]-morpholine 
• 99691-57-3 4-(2-phenyl-nonanoyl)-morpholine 
• 93378-48-4 1-morpholino-2,3-diphenylpropan-1-one 
• 93814-15-4 4-(5-dimethylamino-2-phenyl-pentanoyl)-morpholine 
• 94431-81-9 4-(5-diethylamino-2-phenyl-pentanoyl)-morpholine 
• 92912-55-5 N-phenylacetyl-3-methoxymorpholine 
• 33489-10-0 (2R,3R)-1,5-Di-morpholin-4-yl-2,3-diphenyl-pentane-1,5-dione 
• 33489-10-0 (2R,3S)-1,5-Di-morpholin-4-yl-2,3-diphenyl-pentane-1,5-dione 
• 33489-08-6 (3R,4R)-5-Morpholin-4-yl-5-oxo-3,4-diphenyl-pentanoic acid diethylamide 
• 33489-08-6 (3S,4R)-5-Morpholin-4-yl-5-oxo-3,4-diphenyl-pentanoic acid diethylamide 
• 31576-84-8 4-(6-chloro-3,4-diphenyl-2-quinolyl)morpholine 
• 135181-95-2 4-(3,4-diphenyl-2-quinolyl)morpholine 

Relevant articles and documents

Mechanistic Elucidation of Zirconium-Catalyzed Direct Amidation

The mechanism of the zirconium-catalyzed condensation of carboxylic acids and amines for direct formation of amides was studied using kinetics, NMR spectroscopy, and DFT calculations. The reaction is found to be first order with respect to the catalyst and has a positive rate dependence on amine concentration. A negative rate dependence on carboxylic acid concentration is observed along with S-shaped kinetic profiles under certain conditions, which is consistent with the formation of reversible off-cycle species. Kinetic experiments using reaction progress kinetic analysis protocols demonstrate that inhibition of the catalyst by the amide product can be avoided using a high amine concentration. These insights led to the design of a reaction protocol with improved yields and a decrease in catalyst loading. NMR spectroscopy provides important details of the nature of the zirconium catalyst and serves as the starting point for a theoretical study of the catalytic cycle using DFT calculations. These studies indicate that a dinuclear zirconium species can catalyze the reaction with feasible energy barriers. The amine is proposed to perform a nucleophilic attack at a terminal η2-carboxylate ligand of the zirconium catalyst, followed by a C-O bond cleavage step, with an intermediate proton transfer from nitrogen to oxygen facilitated by an additional equivalent of amine. In addition, the DFT calculations reproduce experimentally observed effects on reaction rate, induced by electronically different substituents on the carboxylic acid.

Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines

A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.