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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.

white crystalline powder

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.

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.

ChEBI: The monoamide of oxalic acid.

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