1871-89-2

Basic information

• Product Name: N,N'-Bis(2-hydroxyethyl)oxamide
• Synonyms: S-DIETHANOLOXAMIDE;TIMTEC-BB SBB008397;N,N'-OXALYLBIS(ETHANOLAMINE);N,N'-BIS(2-HYDROXYETHYL)OXAMIDE;N,N'-DIETHANOLOXAMIDE;Ethanediamide, N,N'-bis(2-hydroxyethyl)-;n,n’-bis(2-hydroxyethyl)-ethanediamid;N,N'-bis(2-hydroxyethyl)ethanediamide
• CAS NO: 1871-89-2
• Molecular Formula: C₆H₁₂N₂O₄
• Molecular Weight: 176.17
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 1871-89-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 168 °C (dec.)(lit.)
• Appearance: /
• Density: 1.31 g/cm³
• Refractive Index: 1.509
• Water Solubility: Insoluble in water.
• Sensitive: Hygroscopic
• CAS DataBase Reference: N,N'-Bis(2-hydroxyethyl)oxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(2-hydroxyethyl)oxamide(1871-89-2)
• EPA Substance Registry System: N,N'-Bis(2-hydroxyethyl)oxamide(1871-89-2)

Safety Data

• Hazard Codes: T,Xi
• Statements: 43
• Safety Statements: 45-36/37
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1871-89-2(Hazardous Substances Data)

Usage

Description

N,N'-Bis(2-hydroxyethyl)oxamide, also known as Diethoxamide, is an organic compound that serves as a crucial intermediate in various chemical syntheses. It is characterized by its amide functional group and two hydroxyethyl substituents, which contribute to its reactivity and versatility in different applications.

Uses

Used in Organic Synthesis:
N,N'-Bis(2-hydroxyethyl)oxamide is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows it to participate in a range of reactions, such as condensation, substitution, and rearrangement, leading to the formation of diverse chemical products.
Used in Pharmaceuticals:
In the pharmaceutical industry, N,N'-Bis(2-hydroxyethyl)oxamide is utilized as a building block for the development of new drugs. Its ability to form hydrogen bonds and interact with other functional groups makes it a valuable component in the design of pharmaceutical molecules with specific biological activities.
Used in Agrochemicals:
N,N'-Bis(2-hydroxyethyl)oxamide is employed as a starting material in the production of agrochemicals, such as pesticides and herbicides. Its chemical properties enable the creation of compounds that can effectively target and control pests and weeds in agricultural settings.
Used in Dyestuff:
In the dyestuff industry, N,N'-Bis(2-hydroxyethyl)oxamide is used as a raw material for the synthesis of various dyes and pigments. Its reactivity and compatibility with other chemical components facilitate the development of colorants with desired properties, such as color intensity, stability, and solubility.

InChI:InChI=1/C6H12N2O4/c9-3-1-7-5(11)6(12)8-2-4-10/h9-10H,1-4H2,(H,7,11)(H,8,12)

Upstream product

• 471-46-5 Oxalamide 
• 141-43-5 ethanolamine 
• 816-27-3 ethyl 2-ethoxy-2-iminoacetate 
• 95-92-1 oxalic acid diethyl ester 
• 540-51-2 2-bromoethanol 
• 40227-15-4 N,N'-diacetyl-oxalamide 
• 148705-17-3 diisopropenyl oxalate 
• 553-90-2 Dimethyl oxalate 
• 120-86-5 N,N'-bis(2-hydroxyethyl)dithiooxamide 
• 2050-60-4 di-n-butyl oxalate 

Downstream Products

• 40651-66-9 C₆H₈Cl₂N₄O₄ 
• 36697-72-0 4,4′,5,5′-Tetrahydro-2,2′-bioxazole 
• 14484-06-1 N-(2-hydroxyethyl)-1H-benzimidazole-2-carboxamide 
• 62209-60-3 N,N'-bis(2-nitrooxyethyl)-N,N'-dinitrooxalamide 
• 98485-17-7 N,N'-bis(2-nitrooxyethyl)oxalamide 
• 16813-43-7 N,N'-bis-(2-chloro-ethyl)-oxalamide 

Relevant articles and documents

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β-oxalylamino-substituted O-ethyl N-arylcarbamates and N-ethyl-N′-arylureas encapsulated into micelles of vinylimidazole–vinylcaprolactam copolymer

Low-molecular-weight compounds—β-oxalylamino-substituted O-ethyl carbamates and unsymmetrical ureas showing biological activity—have been synthesized and encapsulated into micelles of vinylimidazole–vinylcaprolactam copolymers. Solubilization in micelles has provided a preparation of water-soluble colloidal formulation of these compounds suitable for practical application.

Reactivity of β-amino alcohols against dialkyl oxalate: Synthesis and mechanism study in the formation of substituted oxalamide and/or morpholine-2,3-dione derivatives

The reactivity of various β-amino alcohols with dialkyl oxalates, in several reaction conditions, has been investigated. Linear disubstituted oxalamides were obtained with primary β-amino alcohols and linear tetrasubstituted oxalamides, or a mixture of linear tetrasubstituted oxalamides and cyclic morpholine-2,3-diones were obtained with N-substituted β-amino alcohols. A DFT study of the possible mechanism has been made. The theoretical results indicate that these reactions are not kinetically controlled, there is an equilibrium between all species and therefore follow a thermodynamic control. The different behavior between the primary β-amino alcohols and N-methyl β-amino alcohols is due to the greater stability of linear disubstituted oxalamides with respect to linear tetrasubstituted oxalamides. The energy of tetrasubstituted oxalamides is closer to the energy of the corresponding morpholine-2,3-diones.

Method for the synthesis of amides and related products from esters or ester-like compounds

A versatile, eco-friendly, and efficient method for the convenient conversion of esters and ester-like compounds into amides, peptides, carbamates, ureas, oxamides, oxamates, hydrazides, oxazolidinones, pyrazolones, oxazolidinediones, barbituric acids, and other molecules containing one or more OCN moieties in the presence of a diol or polyol is disclosed.