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Oxamide

Also known as Ethanediamide, Oxalamide, Oxamimidic acid, Oxalic acid diamide

Oxamide, also known as ethanediamide or oxalamide, is a nitrogen-rich oxalic acid diamide used primarily in research, chemical synthesis and materials-development work.

Organic chemicals Carboxylic acid diamides
C₂H₄N₂O₂
C₂H₄N₂O₂

Product identity

CAS number
471-46-5
Molecular formula
C2H4N2O2
Molecular weight
88.07 g/mol
Category
Organic chemicals
Subcategory
Carboxylic acid diamides
Common aliases
Ethanediamide, Oxalamide, Oxamimidic acid

Product overview

What is Oxamide?

Oxamide is the neutral diamide of oxalic acid, also called ethanediamide, oxalamide, oxamimidic acid, oxalic acid diamide or diaminoglyoxal. Its chemical identity is fixed by CAS 471-46-5 and molecular formula C2H4N2O2. With a molecular weight of 88.07, the molecule contains two amide groups linked across a two-carbon oxalyl framework, giving it a compact, nitrogen- and oxygen-rich composition.

Oxamide is a polar, hydrogen-bonding solid whose paired amide groups strongly influence crystal packing and intermolecular association. Those interactions help explain its limited compatibility with many ordinary organic solvents and its tendency to behave differently from more readily dissolved oxalic acid derivatives. Its response to heat, acids, bases and reactive coupling partners depends on the surrounding medium, temperature and contact time.

In established chemical work, Oxamide serves mainly as a research compound, an intermediate or nitrogen-containing building block, and a subject for studies of hydrogen bonding, thermal behaviour and coordination chemistry. It may also appear in exploratory materials and polymer research where a compact diamide structure is useful. A particular grade should be assessed for the intended synthesis, analytical method or formulation before technical adoption.

Selection of Oxamide should reflect the required identity, physical form, impurity profile, particle characteristics and compatibility with the planned process. Solubility limitations can affect charging, sampling, reaction uniformity and analytical preparation, while strong intermolecular bonding can influence dispersion and thermal response. Users should evaluate the specific material against their own methods and applicable workplace controls rather than infer suitability from the name alone. For commercial selection, the compound name should be considered separately from the specification and supplied form required for the intended process.

Technical profile

Product properties

Review the product identity and general physical profile before specifying the grade required for your operation.

Category
Organic chemicals
Subcategory
Carboxylic acid diamides
IUPAC name
oxamide
Molecular formula
C2H4N2O2
Molecular weight
88.07 g/mol

Uses and markets

Applications and industries

The correct product specification depends on the intended process, grade requirements and operating conditions.

Detailed product information

Detailed Oxamide product information

Molecular structure and hydrogen bonding

Oxamide contains two amide functions joined through an oxalyl unit. This arrangement creates a strongly polar molecular surface and multiple hydrogen-bond donors and acceptors. In the solid state, these sites can organize neighbouring molecules into persistent intermolecular networks, making crystal packing an important part of its observed behaviour. The structure is therefore relevant to spectroscopy, crystallography and comparative studies of small diamides.

Compared with urea, Oxamide has a carbon–carbon linkage between its carbonyl groups rather than a single carbonyl centre bonded to two amino groups. Compared with oxalic acid, Oxamide replaces both acidic hydroxyl groups with amide groups, changing acidity, hydrogen bonding and reaction behaviour. These distinctions matter when selecting reference compounds, predicting solvent response or interpreting analytical results in mixed systems.

Solubility, thermal response and reactivity

Oxamide’s strong intermolecular association commonly makes dissolution more demanding than for many smaller, less extensively hydrogen-bonded organic compounds. Solvent choice, temperature, particle size and mixing can all influence the time required to obtain a uniform preparation. Analytical work should distinguish true dissolution from suspension or slow equilibration, particularly when concentration is calculated from a visually clear endpoint alone.

As a diamide, Oxamide can participate in transformations involving hydrolysis, condensation or derivatisation under suitable chemical conditions. Its response is not defined solely by the presence of nitrogen and oxygen; pH, water activity, catalysts and heating history may alter the pathway. Compared with oxalic acid, it is generally treated as a neutral amide rather than a dicarboxylic acid, so acid–base handling and reaction planning differ substantially.

Established research and process roles

Oxamide is most defensibly positioned in research, analytical development and chemical synthesis where a compact nitrogen-rich diamide is required or being studied. Researchers may investigate its crystal structure, hydrogen-bonding patterns, thermal transitions, decomposition behaviour or interactions with metals and other polar species. It can also serve as a model compound when comparing amide-rich molecules with related oxalic-acid derivatives.

In process development, Oxamide may function as an intermediate, reactant or compositional component in an experimentally defined route. Its usefulness depends on reaction conversion, isolation behaviour, compatibility with solvents and the downstream purpose of the product. It should not be assumed to provide the same performance as urea, oxalic acid or other diamides, because functional-group placement and solid-state behaviour can change the practical outcome.

Analytical and formulation considerations

Identity work for Oxamide can draw on complementary techniques such as infrared spectroscopy, nuclear magnetic resonance, elemental analysis, chromatography where method-compatible, thermal analysis and diffraction-based examination. The selected combination should address the possibility of residual solvent, moisture, unreacted starting materials or related nitrogen-containing compounds. A single measurement may not distinguish every structurally similar impurity or physical form.

Formulation and sample preparation should account for Oxamide’s polarity, limited solvent compatibility and tendency toward hydrogen-bonded aggregation. Milling, wetting, heating or pH adjustment may change the preparation without changing the nominal molecular identity. Comparisons with urea or oxalic acid are useful only when the method controls concentration, water content and matrix effects, since apparent differences may reflect preparation rather than intrinsic chemistry.

Frequently asked questions

Questions about Oxamide

What is Oxamide, and how is it structurally classified?

Oxamide is the diamide derived from oxalic acid and is also known as ethanediamide or oxalamide. Its molecule contains two amide groups connected through a two-carbon oxalyl framework. That structure gives Oxamide a compact, polar composition with several sites capable of hydrogen bonding. It is classified as a neutral organic diamide rather than as a dicarboxylic acid, even though oxalic acid is its parent acid. The distinction affects acidity, solubility and reaction behaviour. Oxamide is commonly encountered in research, analytical development and chemical synthesis, where its functional groups and solid-state properties are more important than any single commercial use.

Why can Oxamide be difficult to dissolve?

Oxamide can be difficult to dissolve because its two amide groups create strong intermolecular hydrogen bonding in the solid state. Energy is therefore required to separate molecules from the crystal lattice before solvent interactions can stabilise them. Solvent polarity alone does not predict the result perfectly; hydrogen-bonding ability, temperature, particle size, mixing and water content also matter. A cloudy or slowly clearing preparation may represent a suspension, partial dissolution or delayed equilibration rather than a fully dissolved sample. For analytical work, users should establish a preparation method experimentally and confirm that the chosen solvent and concentration range provide reproducible results.

How does Oxamide differ from urea?

Oxamide and urea are both nitrogen-rich amides, but their structures are different. Urea has one carbonyl carbon bonded to two amino groups, whereas Oxamide contains two carbonyl groups connected by a carbon–carbon bond, with one amino group associated with each carbonyl. This difference changes molecular size, hydrogen-bonding geometry, crystal packing, solubility and thermal behaviour. Consequently, urea should not automatically be used as a performance substitute or analytical surrogate for Oxamide. The appropriate comparison depends on the purpose: reaction design, spectroscopy, crystallisation, thermal testing and formulation may each reveal different distinctions between the compounds.

What types of research commonly involve Oxamide?

Oxamide can be relevant to several research areas because it combines two amide functions within a small molecule. Studies may examine its crystal structure, hydrogen-bonding networks, thermal response, decomposition pathways, coordination with metals or behaviour as a nitrogen-containing synthetic intermediate. It may also be included in exploratory polymer and materials investigations where polar diamide groups are useful for studying intermolecular association. These are research contexts rather than a guarantee of suitability for a finished product. The actual role of Oxamide depends on the reaction design, analytical method, physical form and performance criteria established by the investigator.

Can Oxamide be hydrolysed or chemically transformed?

Oxamide can undergo chemical transformation under suitable conditions, including reactions associated with amide hydrolysis or derivatisation. The rate and products depend on factors such as acid or base strength, temperature, water availability, catalysts, concentration and reaction time. Because its two amide groups are connected within an oxalyl framework, the pathway may differ from that of urea, oxalic acid or a simple monoamide. Heating alone should not be treated as a predictable conversion method, since thermal behaviour can include competing processes. Any proposed transformation should be established experimentally with appropriate analytical monitoring and process controls.

What should be considered when analysing Oxamide in a formulation or reaction mixture?

Analysis of Oxamide should consider its limited solvent compatibility, strong hydrogen bonding and possible association with other polar ingredients. Sample preparation must establish whether the material is fully dissolved, evenly suspended or undergoing slow equilibration. Matrix components can affect extraction, spectroscopy, chromatography and thermal measurements, while moisture may influence both handling and apparent composition. A robust evaluation may combine orthogonal techniques, such as spectroscopic identity testing with chromatographic, elemental or thermal measurements, according to the application. Results should be interpreted against suitable Oxamide references and method-specific controls rather than against urea or oxalic acid by default.

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