20538-39-0

Basic information

• Product Name: 1-methyl-3,3-diphenylpyrrolidin-2-one
• CAS NO: 20538-39-0
• Molecular Formula: C₁₇H₁₇NO
• Molecular Weight: 251.323
• Mol File: 20538-39-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 412.3°C at 760 mmHg
• Flash Point: 168.1°C
• Density: 1.126g/cm³
• Vapor Pressure: 5.24E-07mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 1-methyl-3,3-diphenylpyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-3,3-diphenylpyrrolidin-2-one(20538-39-0)
• EPA Substance Registry System: 1-methyl-3,3-diphenylpyrrolidin-2-one(20538-39-0)

Safety Data

• Hazardous Substances Data: 20538-39-0(Hazardous Substances Data)

Usage

Compound class

Pyrrolidinones.

Appearance

Colorless to yellow liquid.

Odor

Sweet, floral.

Usage

Solvent in various industrial applications, such as manufacturing of polymers, adhesives, and coatings.

Application

Intermediate in the production of pharmaceuticals and agrochemicals.

Biological activity

Inhibitor of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) enzymes, making it a target for drug development in the treatment of inflammation and related disorders.

Safety measures

Appropriate safety measures required due to potential health hazards, such as skin and eye irritation, and harmful effects when ingested or inhaled.

Upstream product

• 872-50-4 1-methyl-pyrrolidin-2-one 
• 108-86-1 bromobenzene 
• 23278-88-8 4-dimethylamino-2,2-diphenyl-butyronitrile 
• 86-29-3 Diphenylacetonitrile 
• 591-50-4 iodobenzene 
• 23227-52-3 4-diethylamino-2,2-diphenyl-butyric acid ethyl ester 
• 74-89-5 methylamine 
• 98250-74-9 1-methyl-3,3-diphenyl-pyrrolidin-2-one-imine; hydrochloride 
• 101718-26-7 4-dimethylamino-2,2-diphenyl-butyric acid 
• 956-89-8 3,3-Diphenyl-dihydro-furan-2-one 

Relevant articles and documents

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48-75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.