33744-04-6

Usage

Uses

Versatile intermediate in the production of pharmaceuticals, agrochemicals, and specialty chemicals; chlorination agent in organic synthesis; solvent; industrial bleach

Reactivity

Highly reactive

Importance

Important building block in the synthesis of many important chemical compounds

Safety precautions

Irritant to skin, eyes, and respiratory system; should be handled with caution in industrial or laboratory settings

Upstream product

• 616-45-5 2-pyrrolidinon 
• 1588772-25-1 5-(chloromethyl)-5-methylpyrrolidin-2-one 

Downstream Products

• 616-45-5 2-pyrrolidinon 
• 63853-74-7 5-methoxypyrrolidin-2-one 
• 89736-66-3 1-(1-Methyl-heptyl)-pyrrolidin-2-one 
• 89736-64-1 1-(2-Chloro-octyl)-pyrrolidin-2-one 
• 89736-65-2 1-(1-Chloromethyl-heptyl)-pyrrolidin-2-one 
• 89736-61-8 Acetyl-(2-chloro-octyl)-carbamic acid ethyl ester 
• 89736-55-0 1-((1R,2R)-2-Chloro-cyclohexyl)-pyrrolidin-2-one 
• 89736-55-0 1-((1R,2S)-2-Chloro-cyclohexyl)-pyrrolidin-2-one 

Relevant academic research and scientific papers

Algae-fungicide and algae-sterilization method

This invention relates to an algicide of excellent water solubility, low cost and excellent handling that is characterized in containing N-chloro-2-pyrrolidinone, as well as to an algicidal/microbicidal agent characterized in containing one or more compounds selected from cyclic N-chloro compounds and N,N'-dichloro compounds represented by formula (1). (1) (In the formula, X represents a methylene group, secondary amino group, or N-chloro group, and R represents a C2-5 alkylene group, provided that when X is an N-chloro group, R is a C2-3 alkylene group.)

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

The kinetics of N-chlorination reaction of pyrrolidine, pyrrolidone, succinimide, 5,5,-dimethyloxazolidine-2,4-dione, 5,5-dimethylhydantoin and 1-hydroximethyl-5,5-dimethylhydantoin with HOCl in aqueous solution were studied at 25 °C, constant ionic strength and under isolation conditions in a wide pH range. The set of compounds studied in this paper is characterized by having different functional groups and the same cyclic structure, consisting of a five-member ring with a nitrogen atom in the ring, which is susceptible to be chlorinated. This series of compounds covers nine pKa units, and the kinetic studies allow us to know, like, the presence of an amino, amide or imide group modify the reactivity of nitrogenous compound. Experimental data were fitted to the first-order kinetic equation. All reactions were found to be of first order in both HOCl and nitrogenous compound concentration. Kinetics studies demonstrate that some of these compounds are hydrolyzed in alkaline medium. In each case, reaction mechanism in agreement with the experimental results is proposed. The results were compared with other compounds with similar cyclic structure (2-oxazolidinone and proline). Copyright

Antimicrobial Haloalkyl Heterocycle Compounds

This application describes compounds useful as anti-microbial agents, including as antibacterial, disinfectant, antifungal, germicidal or antiviral agents.

Copper-promoted iodovinylation of amides: synthesis of β-functionalized enamides

We studied the addition of nitrogen radicals to ynol ethers in order to form β-functionalized enamides. Poor yields are reported. On the other hand, we observed that copper coupling between 1,2-diiodoethene and various amides leads to β-functionalized enamides in high yields with complete stereocontrol.

N,N′-dichlorobis(2,4,6-trichlorophenyl)urea (CC-2): An efficient reagent for N-chlorination of amino esters, amide, and peptides

A simple, efficient, and rapid protocol for N-chlorination of various protected amino esters, amides, and peptides has been described. N,N′-dichlorobis(2,4,6-trichlorophenyl)urea has been used as a chlorinating agent and transformation takes place rapidly in mild conditions with quantitative yields. Copyright

A simple protocol for efficient N-chlorination of amides and carbamates

N-Chlorination of various amides, lactams, and carbamates with very cheap trichloroisocyanuric acid proceeds efficiently under very mild conditions. Excellent results were also observed for the N-chlorination of carbamates of free amino acids.

New protocol for efficient N-chlorinations of amides and carbamates

N-Chlorination of various amides, carbamates and lactams with inexpensive and stable calcium hypochlorite on moist alumina proceeds smoothly and efficiently, e.g. the technically important 1-chlorohexahydroazepin-2-one (3-Cl) and 1-chloropyrrolidin-2-one (7-Cl) were obtained in 95 % and 98% yield, respectively. Excellent results were also observed for the N-chlorination of protected amino acid esters with a cyclopropane moiety to give derivatives such as methyl (tert-butoxycarbonylchloroamino)cyclopropylacetate (1-Cl), methyl (benzyloxycarbonylchloroamino)cyclopropylacetate (2-Cl), methyl 1-(tert-butoxycarbonylchloroamino)cyclopropanecarboxylate (5-Cl) and methyl trans-2-(tert-butoxycarbonylchloroamino)cyclopropanecarboxylate (6-Cl) in 99%, 96%, 90% and 97% yield, respectively.