1687-60-1

Basic information

• Product Name: N,N'-dihydroxyoxamide
• Synonyms: N,N'-dihydroxyoxamide;oxalyldihydroxamic acid;1,2-Dihydroxy-1,2-bis(hydroxyimino)ethane;1,2-Dihydroxyethanedial dioxime;Dihydroxyglyoxim;Ethanebishydroxamic acid;Ethanedihydroxamic acid;N,N'-Dihydroxyethanediamide
• CAS NO: 1687-60-1
• Molecular Formula: C₂H₄N₂O₄
• Molecular Weight: 120.06416
• EINECS: 216-874-3
• Mol File: 1687-60-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 82 °C(Solv: benzene (71-43-2))
• Boiling Point: 567.2°Cat760mmHg
• Flash Point: 384.8°C
• Appearance: /
• Density: 1.754g/cm³
• PKA: 6.89±0.23(Predicted)
• CAS DataBase Reference: N,N'-dihydroxyoxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-dihydroxyoxamide(1687-60-1)
• EPA Substance Registry System: N,N'-dihydroxyoxamide(1687-60-1)

Safety Data

• Hazardous Substances Data: 1687-60-1(Hazardous Substances Data)

Usage

General Description

N,N'-dihydroxyoxamide is a chemical compound with the molecular formula C2H6N2O4. Also known as oxalohydroxamic acid, it is a chelating agent used in the treatment of toxic metal poisoning, particularly with uranium and other actinide elements. N,N'-dihydroxyoxamide forms stable complexes with metal ions, thereby preventing their toxic effects on the body. It has also been studied for its potential use in the extraction of rare earth elements from ores and industrial waste streams. In addition, it has applications in analytical chemistry, specifically in the determination of certain metal ions in solution. N,N'-dihydroxyoxamide is a potential alternative to traditional chelating agents and continues to be researched for its various applications in both medical and industrial fields.

Upstream product

• 131543-46-9 Glyoxal 
• 599-71-3 piloty's acid 
• 144-62-7 oxalic acid 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 7803-49-8 hydroxylamine 
• 144-62-7 oxalic acid 
• 5743-07-7 cadmium oxalate trihydrate 
• 959-32-0 N-(benzoyloxy)benzamide 

Relevant articles and documents

14N Quadrupole Double Resonance in Some Substituted Hydroxamic Acids

14N quadrupole coupling constants and asymmetry parameters have been measured in a number of hydroxamic acids by double-resonance field-cycling techniques based on either irradiation in zero magnetic field or cross relaxation.The compounds all display high asymmetry parameters.Those in which this quantity is greater than 0.9 show remarkable line shapes for the two lower 14N frequencies (νy, νz) in their irradiation spectra.They are explained in terms of a thermal-mixing mechanism, which generates polarization of the 1H dipolar levels when these nearly degenerate frequencies are strongly irradiated in zero field, and then subsequently modified by level crossing when the sample is returned to high field to measure the remaining 1H signal.Ab initio SCF-MO calculations of the 14N quadrupole tensor in a group of molecules at the orientation found in crystals of acetohydroxamic acid hemihydrate and oxalodihydroxamic acid are in reasonable agreement with experiment and predict that in all the hydroxamic acids studied the maximum principal component is negative and closely parallel to the direction of the 2p? orbital.

Experimental and computational studies on hydroxamic acids as environmental friendly chelating corrosion inhibitors for mild steel in aqueous acidic medium

In the present study, three hydroxamic acids (HAs) namely acetohydroxamic acid (AHA), benzohydroxamic acid (BHA) and oxalohydroxamic acid (OHA) were synthesized, characterized and used as inhibitors for mild steel corrosion in1 M HCl using chemical, electrochemical, surface and computational methods. Results of the studies show that the HAs act as effective corrosion inhibitors and their inhibition efficiencies follow the order: OHA (96.37%) > BHA (95.69%) > AHA (93.29%). EIS study showed that studied HAs act as interface type inhibitors. Polarization study revealed that HAs demonstrate mixed-type corrosion inhibitors characteristics and adsorb on the active sites of metallic surface. Adsorption of HAs on metal-1 M HCl interfaces followed the Langmuir adsorption isotherm model. Surface morphological analyses of inhibited and uninhibited metallic surface were carried out using SEM-EDX and XRD methods. DFT analyses showed that studied compounds act as chelating type of ligands. Effect of Keto-enol tautomerism and different possible conformational isomers on metallic corrosion inhibition was demonstrated. The conformational isomers in which >C=O and –OH (hydroxyl) groups present in same side behave as chelating ligands and form relatively more stable complex than that of conformational isomers in which >C=O and –OH groups present in opposite side. Experimental and DFT studies complimented each other well.

A comparison between the acid-catalysed reactions of some dihydroxamic acids, monohydroxamic acids and desferal

A kinetic study on the hydrolysis of some dihydroxamic acids HOHNOC-(CH2)n-CONHOH (n = 0, oxalo, [ODHA]; n = 1 malono [MDHA]; and n = 2, succino, [SDHA] dihydroxamic acids) in aqueous mineral acids is reported. A comparison of the kinetic data with those from the hydrolysis of simple monohydroxamic acid, (acetohydroxamic acid [AHA] CH3CONHOH, benzohydroxamic acid [BHA] C6H5CONHOH) and the natural trihydroxamate-based siderophore desferal (DFB) revealed that the hydrolytic stability sequence of the compounds is generally: BHA > ODHA > MDHA > DFB > AHA > SDHA. An excess acidity analysis reveals that the reaction involving a pre-equilibrium protonation was followed by a rate determining A-2 type nucleophilic attack of water molecule on the protonated substrate. An attempt has been made to study protonation equilibria.