5411-58-5

Basic information

• Product Name: ETHYL N,N-DIETHYLOXAMATE
• Synonyms: TIMTEC-BB SBB007933;Ethyl (diethylamino)(oxo)acetate;ETHYL DIETHYL OXAMATE;ETHYL N,N-DIETHYLOXAMATE;N,N-Diethyloxamic acid ethyl ester;NISTC5411585;N,N-Diethyloxamidic acid ethyl ester;2-(diethylamino)-2-keto-acetic acid ethyl ester
• CAS NO: 5411-58-5
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.21
• Mol File: 5411-58-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 218.7°C at 760 mmHg
• Flash Point: 86°C
• Appearance: /
• Density: 1.028g/cm³
• Vapor Pressure: 0.124mmHg at 25°C
• Refractive Index: 1.442
• PKA: -1.34±0.70(Predicted)
• CAS DataBase Reference: ETHYL N,N-DIETHYLOXAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL N,N-DIETHYLOXAMATE(5411-58-5)
• EPA Substance Registry System: ETHYL N,N-DIETHYLOXAMATE(5411-58-5)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• HazardClass: IRRITANT
• Hazardous Substances Data: 5411-58-5(Hazardous Substances Data)

Usage

General Description

ETHYL N,N-DIETHYLOXAMATE is a chemical compound with the molecular formula C7H15NO3. It is a clear, colorless liquid that is insoluble in water but soluble in organic solvents. ETHYL N,N-DIETHYLOXAMATE is used as a corrosion inhibitor and as an intermediate in the synthesis of other chemicals. It is also used as a pesticide and a plant growth regulator. ETHYL N,N-DIETHYLOXAMATE is considered to be low in toxicity, with some potential for skin, eye, and respiratory irritation. It should be handled with care and in accordance with proper safety protocols.

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

Upstream product

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

Downstream Products

• 88584-86-5 N,N-diethyl-2-oxo-3-phenylpropanamide 
• 675120-14-6 3-ethyl-2-methyl-5-methylene-oxazolidin-4-one 
• 497872-29-4 3-ethyl-5-hydroxy-2,5-dimethyl-oxazolidin-4-one 
• 675120-17-9 N,N-diethyl-3-(2-hydroxy-5-methoxy-phenyl)-2-oxo-propionamide 
• 2728-05-4 N,N-Diethyl-p-toluamid 
• 1350443-91-2 C₂₃H₂₉NO₅ 
• 60254-65-1 N,N-Diethyloxamsaeure-hexylester 
• 120313-16-8 N,N-diethyl-3-phenoxy-2-oxopropanamide 
• 96181-24-7 N,N-Diaethyl-cyclohexyl-glyoxylsaeure-amid 
• 95284-61-0 2-Hydroxy-2,2-dicyclohexyl-N,N-diaethyl-acetamid 
• 2644-21-5 ethyl N,N-diethylglycinate 
• 617-84-5 N-formyldiethylamine 
• 10049-90-8 N,N-diethyl-α-hydroxy-α-phenylbenzeneacetamide 
• 34906-86-0 N,N-diethyl-2-oxo-2-phenylacetamide 

Relevant articles and documents

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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.

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.