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Oxamic acid

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Oxamic acid Basic information

Product Name:
Oxamic acid
Synonyms:
  • AMINOOXOACETIC ACID
  • Oxamic acid Oxalic acid monoamide
  • Oxamicacid,98%
  • Aminooxoacetic acid, Oxalic acid monoamide
  • OxaMic acid, 98% 10GR
  • OxaMic acid, 98% 25GR
  • 2-aMino-2-oxoacetic acid
  • Acetic acid, aminooxo-
CAS:
471-47-6
MF:
C2H3NO3
MW:
89.05
EINECS:
207-443-0
Mol File:
471-47-6.mol
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Oxamic acid Chemical Properties

Melting point:
207-210 °C (dec.) (lit.)
Boiling point:
165.08°C (rough estimate)
Density 
1.6193 (rough estimate)
refractive index 
1.4264 (estimate)
storage temp. 
2-8°C(protect from light)
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form 
Crystalline Powder
pka
1.60±0.20(Predicted)
color 
White
Water Solubility 
Soluble in water 108 mg/mL.
Merck 
14,6917
BRN 
1743294
InChI
InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6)
InChIKey
SOWBFZRMHSNYGE-UHFFFAOYSA-N
SMILES
C(O)(=O)C(N)=O
CAS DataBase Reference
471-47-6(CAS DataBase Reference)
EPA Substance Registry System
Oxamic acid (471-47-6)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
TSCA 
Yes
HS Code 
29241990

MSDS

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Oxamic acid Usage And Synthesis

Description

Oxamic acids also known to as oxalic acid monoamides have emerged as potent precursors for the generation of the carbamoyl radical. Oxamic acids can easily undergo decarboxylation through a single electron oxidation resulting in the generation of the reactive carbamoyl radical, which can then engage in diverse radical reactions or undergo a second single electron oxidation as originally unveiled by Minisci. Oxamic acids are thus versatile intermediates for the synthesis of nitrogen-containing organic molecules[1]. The oxidative decarboxylation of oxamic acids can be mediated through thermal, photochemical, electrochemical or photoelectrochemical means, generating carbamoyl radicals, which may further add to unsaturated systems to provide a broad range of important amides. Oxidative decarboxylation of oxamic acids also offers a straightforward entry for the preparation of urethanes, ureas, and thioureas.

Chemical Properties

Oxamic acid is a white, water-soluble solid. It is the monoamide ofoxalic acid. It can react with metal carbonates to form oxamate. Oxamic acid inhibits lactate dehydrogenase A.

Uses

Oxamic acid is an ozone oxidation product and is used in the synthesis of hydroxybenzimidazoles preparation as potential anti tumor agents targeting human lactate dehydrogenase A.This compound is suitable for lactate dehydrogenase (LDH) related research.

Application

Oxamic acid (OA) has applications in polymer chemistry. It increases the water solubility of certain polymers, including polyester,epoxide, and acrylic upon binding with them. Oxamic acid can be used as a reactant to prepare 6-phenanthridinecarboxamide by direct C-H carbamoylation reaction using ammonium persulfate in DMSO. It can also be used as an organic ligand to prepare functionalized metal oxide nanoparticles for various biological applications. OA along with p-aminobenzoic acid is used to functionalize Au nanoparticles for the development of a sensor to detect Fe3+ ions by the calorimetric method.

Definition

ChEBI: Oxamic acid is a dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia. It has a role as an Escherichia coli metabolite. It is a conjugate acid of an oxamate.

References

[1] Ikechukwu Martin Ogbu . “Oxamic acids: useful precursors of carbamoyl radicals.” Chemical Communications 58 55 (2022): Pages 7593-7607.

Oxamic acid Preparation Products And Raw materials

Raw materials

Oxamic acidSupplier

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