5411-58-5

Usage

Uses

Used in Chemical Synthesis:
ETHYL N,N-DIETHYLOXAMATE is utilized as an intermediate in the synthesis of other chemicals, playing a crucial role in the production of various compounds for different applications.
Used in Corrosion Inhibition:
As a corrosion inhibitor, ETHYL N,N-DIETHYLOXAMATE helps protect materials from the damaging effects of corrosion, extending their service life and improving their performance in various industries.
Used in Pesticide Formulation:
ETHYL N,N-DIETHYLOXAMATE is employed as a component in pesticides, contributing to the control of pests and the protection of crops and other plants.
Used in Plant Growth Regulation:
ETHYL N,N-DIETHYLOXAMATE also serves as a plant growth regulator, aiding in the management of plant growth and development to optimize agricultural productivity.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its chemical properties and uses, it is plausible that ETHYL N,N-DIETHYLOXAMATE could also be used in the pharmaceutical industry as an intermediate for the synthesis of pharmaceutical compounds or as a component in drug formulations.
It is important to handle ETHYL N,N-DIETHYLOXAMATE with care and follow proper safety protocols to minimize the risk of irritation or other adverse effects.

InChI:InChI=1/C8H15NO3/c1-4-9(5-2)7(10)8(11)12-6-3/h4-6H2,1-3H3

Upstream product

• 109-89-7 diethylamine 
• 95-92-1 oxalic acid diethyl ester 
• 515-84-4 Ethyl trichloroacetate 
• 121-44-8 triethylamine 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 541-41-3 chloroformic acid ethyl ester 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

• 617-84-5 N-formyldiethylamine 
• 88584-86-5 N,N-diethyl-2-oxo-3-phenylpropanamide 
• 3004-58-8 N,N-diethyl-2,2-diphenylacetamide 
• 2728-05-4 N,N-Diethyl-p-toluamid 
• 1350443-91-2 C₂₃H₂₉NO₅ 
• 248602-69-9 (E)-3-(Dimethoxyphosphoryl)-N,N-diethyl-4-(4-nitrophenyl)-2-oxobut-3-enamide 
• 675120-17-9 N,N-diethyl-3-(2-hydroxy-5-methoxy-phenyl)-2-oxo-propionamide 
• 497872-29-4 3-ethyl-5-hydroxy-2,5-dimethyl-oxazolidin-4-one 
• 675120-14-6 3-ethyl-2-methyl-5-methylene-oxazolidin-4-one 

Relevant academic research and scientific papers

Analogues of the Herbicide, N-Hydroxy- N-isopropyloxamate, Inhibit Mycobacterium tuberculosis Ketol-Acid Reductoisomerase and Their Prodrugs Are Promising Anti-TB Drug Leads

New drugs to treat tuberculosis (TB) are urgently needed to combat the increase in resistance observed among the current first-line and second-line treatments. Here, we propose ketol-acid reductoisomerase (KARI) as a target for anti-TB drug discovery. Twenty-two analogues of IpOHA, an inhibitor of plant KARI, were evaluated as antimycobacterial agents. The strongest inhibitor of Mycobacterium tuberculosis (Mt) KARI has a Ki value of 19.7 nM, fivefold more potent than IpOHA (Ki = 97.7 nM). This and four other potent analogues are slow- and tight-binding inhibitors of MtKARI. Three compounds were cocrystallized with Staphylococcus aureus KARI and yielded crystals that diffracted to 1.6-2.0 ? resolution. Prodrugs of these compounds possess antimycobacterial activity against H37Rv, a virulent strain of human TB, with the most active compound having an MIC90 of 2.32 ± 0.04 μM. This compound demonstrates a very favorable selectivity window and represents a highly promising lead as an anti-TB agent.

One-Pot Synthesis of Tertiary Amides from Organic Trichlorides through Oxygen Atom Incorporation from Air by Convergent Paired Electrolysis

A convergent paired electrolysis catalyzed by a B12 complex for the one-pot synthesis of a tertiary amide from organic trichlorides (R-CCl3) has been developed. Various readily available organic trichlorides, such as benzotrichloride and its derivatives, chloroform, dichlorodiphenyltrichloroethane (DDT), trichloro-2,2,2-trifluoroethane (CFC-113a), and trichloroacetonitrile (CNCCl3), were converted to amides in the presence of tertiary amines through oxygen incorporation from air at room temperature. The amide formation mechanism in the paired electrolysis, which was mediated by a cobalt complex, was proposed.

Pd/C-catalyzed synthesis of oxamates by oxidative cross double carbonylation of alcohols and tertiary amines through C-N bond cleavage

An efficient synthesis of oxamates by Pd/C-catalyzed oxidative cross double carbonylation of alcohols and unactivated tertiary amines has been demonstrated. The in situ oxidative C-N bond cleavage of tertiary amines was achieved using molecular oxygen as an environmentally benign oxidant providing a user-friendly approach to the synthesis of oxamates. The developed protocol showed excellent activity towards the cyclic as well as aliphatic tertiary amines and long-chain alcohols. This developed protocol system is advantageous, as it is phosphine ligand free, base free, and copper-free and the Pd/C catalyst is easily recyclable. The Pd/C catalyst was recycled up to five consecutive cycles.

Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B12 Model Complex under Aerobic Conditions

A visible light responsive catalytic system with the B12 complex as the catalyst and [Ir(dtbbpy)(ppy)2]PF6 as the photosensitizer was developed. It provides a convenient and efficient way to synthesize amides. Based on this method, trichlorinated organic compounds were converted into amides in the presence of an amine under aerobic conditions at room temperature in a one-pot procedure. Various trichlorinated organic compounds and an amine source, such as primary, secondary, and cyclic amines, have been evaluated for this transformation, providing the expected products in moderate to excellent yields. Notably, product formation depended on the reaction atmosphere where the amide was obtained under aerobic conditions while partially dechlorinated products were obtained under anaerobic conditions. As this protocol is free from hazardous reagents, extra additives, noble metals, and dangerous gas, the present method provides a novel and efficient approach for amide synthesis under mild and easily controlled conditions.

Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis

Enabled by merging iridium photoredox catalysis and palladium catalysis, α-oxocarboxylate salts can be decarboxylatively coupled with aryl halides to generate aromatic ketones and amides at room temperature. DFT calculations suggest that this reaction proceeds through a Pd0-PdII-PdIII pathway, in which the PdIII intermediate is responsible for reoxidizing IrII to complete the IrIII-IrIII-IrII photoredox cycle. Like a mergin': Enabled by merging iridium photoredox catalysis and palladium catalysis, palladium-catalyzed decarboxylative coupling of α-oxocarboxylates with aryl halides can proceed at room temperature. DFT calculations suggest that a Pd0-PdII-PdIII catalytic cycle is merged with an IrIII-IrIII-IrII photoredox cycle, in which PdIII is responsible for oxidizing IrII to complete the photoredox cycle.

Pd/C-catalyzed synthesis of oxamates by oxidative cross double carbonylation of amines and alcohols under Co-catalyst, base, dehydrating agent, and ligand-free conditions

This work reports a mild, efficient, and ligand-free Pd/C-catalyzed protocol for the oxidative cross double carbonylation of amines and alcohols. Notably, the reaction does not requires any base, co-catalyst, dehydrating agent, or ligand. Pd/C solves the problem of catalyst recovery, and the catalyst was recycled up to six times.

Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety

A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by 1H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics.

Environmentally friendly transesterification and transacylation reactions under libr catalysis

A room-temperature, convenient transesterification of various esters, induced by catalytic amounts of lithium bromide and diethylamine in a solvent-free environment, is described. Products are obtained in good purity by simple filtration to remove the catalyst and evaporation of the volatile portion. The procedure has also been successfully applied to transacetylation and aminolysis of esters. Springer-Verlag 2010.

Synthesis and first X-ray structures of cobalt(II) and cobalt(III) complexes bearing 2,4-dioxo-alkanoic acid dialkylamide ligands

The aerobic oxidation of 5-hydroxy pentenes to trans-tetrahydrofurans (THFs), the Mukaiyama oxidation, has in recent years emerged as a powerful tool in synthetic chemistry. In this report we describe the first crystal structures of 2,4-dioxo-alkanoic acid dialkylamide complexes for both Co(II) and Co(III) salts. The Co(II) structures show an unprecedented arrangement of atoms, with a central Co(II)(H2O)6 flanked by two Co(II) atoms each coordinated with three anionic chelating ligands. The dimeric Co(III) structures show two anionic chelating ligands and bridging hydroxyl groups.

1,8-Naphthyridines VI. Synthesis and anti-inflammatory activity of 5-(alkylamino)-N,N-diethyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides with a new substitution pattern on the triazole ring

On the basis of the good anti-inflammatory properties shown by the 9-alkyl-N,N-dialkyl-5-(alkylamino)[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides 1, a series of analogues of such compounds, in which the 9-alkyl substituent was replaced by an ester or amide group (compounds 3a-i), was prepared and tested (inhibition of carrageenan-induced paw edema in the rat). Also two 5-(N-alkyl,N-acylamino) derivatives (compounds 4a,b) were synthesized and evaluated for the same purpose. Even though the general trend for these new [1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives was a decrease in activity compared with compounds 1, some of the new synthesized compounds exhibited still good anti-inflammatory properties.