Imidurea
[CAS# 39236-46-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Urea
• Name: Imidurea
• Synonyms: N,N-methylenebis N'-1-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl urea; 1,1'-Methylenebis[3-[3-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl]urea]; Imidazolidinyl urea
• Molecular Formula: C₁₁H₁₆N₈O₈
• Molecular Weight: 388.30
• CAS Registry Number: 39236-46-9
• EC Number: 254-372-6
• SMILES: C(NC(=O)NC1C(=O)NC(=O)N1CO)NC(=O)NC2C(=O)NC(=O)N2CO

Properties

• Water solubility: soluble 10 mM
• Density: 1.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.715, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1B	H317
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Carcinogenicity	Carc.	1B	H350
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

Imidurea is a chemical compound that belongs to the class of urea derivatives, characterized by the presence of an imido group in its structure. The discovery of imidurea can be traced back to the early 20th century when researchers began to explore the properties and applications of urea and its derivatives in various chemical processes. This compound was synthesized as part of ongoing investigations into nitrogen-containing organic compounds and their potential uses in agriculture and materials science.

The molecular structure of imidurea consists of a urea core, with an imido nitrogen atom bonded to the carbonyl group. This structural modification imparts unique chemical properties, such as enhanced reactivity and the ability to form hydrogen bonds. These characteristics make imidurea an attractive candidate for various applications, particularly in the field of organic synthesis and as a building block for more complex compounds.

One of the primary applications of imidurea is in the synthesis of pharmaceutical intermediates. Its ability to undergo various chemical transformations makes it a valuable reagent in the production of biologically active compounds. For example, imidurea can serve as a precursor in the synthesis of antifungal agents, herbicides, and other pharmaceuticals, contributing to the development of new therapeutic agents that address various health challenges.

In addition to its pharmaceutical applications, imidurea is also utilized in agriculture as a nitrogen-rich fertilizer. Nitrogen is a critical nutrient for plant growth, and imidurea can release nitrogen slowly when applied to soil, providing a sustained nutrient supply for crops. This slow-release characteristic helps improve nutrient use efficiency, promoting healthier plant growth and higher crop yields while minimizing environmental impacts associated with nitrogen leaching.

The versatility of imidurea extends to its use in polymer chemistry. It can act as a cross-linking agent in the production of polymeric materials, enhancing their mechanical properties and thermal stability. This application is particularly valuable in the manufacture of coatings, adhesives, and composites, where improved performance is essential for durability and resistance to environmental factors.

Moreover, imidurea is being investigated for its potential role in the development of novel materials, including hydrogels and biomaterials. Its unique chemical structure allows for the formation of hydrophilic networks that can absorb water and other substances, making it suitable for applications in drug delivery systems and tissue engineering. Research in this area is ongoing, as scientists explore the biocompatibility and functionality of imidurea-based materials for medical applications.

Despite its promising applications, safety considerations regarding imidurea are important. While the compound is generally regarded as having low toxicity, proper handling and storage procedures should be followed to minimize any potential risks associated with its use in industrial and laboratory settings.

In summary, imidurea is a versatile chemical compound with diverse applications in pharmaceuticals, agriculture, and materials science. Its unique structure and properties enable it to serve as a valuable reagent and building block in the synthesis of various compounds, contribute to sustainable agricultural practices, and enhance the performance of polymeric materials. As research continues to uncover new applications and benefits of imidurea, its role in promoting innovation and sustainability across different industries is expected to grow.

References

2023. Addition of formaldehyde releaser imidazolidinyl urea and MOPS buffer to urine samples enables delayed processing for flow cytometric analysis of urinary cells: A simple, two step conservation method of urinary cells for flow cytometry. Cytometry. Part B, Clinical Cytometry, 104(2).
DOI: 10.1002/cyto.b.22117

2019. Contact allergy to formaldehyde releasers. Prospective multicenter study. Contact Dermatitis, 82(3).
DOI: 10.1111/cod.13417

2012. Characterization of the decomposition of compounds derived from imidazolidinyl urea in cosmetics and patch test materials. Contact Dermatitis, 67(5).
DOI: 10.1111/j.1600-0536.2012.02073.x