40321-44-6

Basic information

• Product Name: 2-oxopyrrolidine-1-carbaldehyde
• Synonyms: 1-pyrrolidinecarboxaldehyde, 2-oxo-; 2-Oxopyrrolidine-1-carbaldehyde
• CAS NO: 40321-44-6
• Molecular Formula: C₅H₇NO₂
• Molecular Weight: 113.1146
• Mol File: 40321-44-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 189.6°C at 760 mmHg
• Flash Point: 79.6°C
• Density: 1.365g/cm³
• Vapor Pressure: 0.566mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 2-oxopyrrolidine-1-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxopyrrolidine-1-carbaldehyde(40321-44-6)
• EPA Substance Registry System: 2-oxopyrrolidine-1-carbaldehyde(40321-44-6)

Safety Data

• Hazardous Substances Data: 40321-44-6(Hazardous Substances Data)

Upstream product

• 120-94-5 1-Methylpyrrolidine 
• 616-45-5 2-pyrrolidinon 
• 26944-31-0 N,N-Diformylacetamide 
• 2258-42-6 formyl acetic anhydride 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 67-56-1 methanol 
• 141-53-7 sodium formate 
• 132150-49-3 1-(1-hydroxy-2-oxo-2-phenylethyl)pyrrolidin-2-one 

Downstream Products

• 616-45-5 2-pyrrolidinon 

Relevant articles and documents

CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides

Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).

Fast and efficient one step synthesis of dienamides

A fast and efficient one-step approach to the synthesis of dienamides is reported. This concise methodology relies on the use of imides as reactive intermediates and allows for the preferential formation of Z,E-dienamides in good yields.

A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional β- and γ-lactams, can be employed.