Glycoluril

Glycoluril

Names
IUPAC name Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
Other names Acetylenediurea; Acetyleneurea; Acetylenediureine; Acetylene carbamide; Glyoxalbiuret; Glyoxaldiureine; Glyoxaldiurene
Identifiers
CAS Number	496-46-8
3D model (Jmol)	Interactive image
ChemSpider	56138
ECHA InfoCard	100.007.111
PubChem	62347
InChI InChI=1S/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10) Key: VPVSTMAPERLKKM-UHFFFAOYSA-N InChI=1/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10) Key: VPVSTMAPERLKKM-UHFFFAOYAG
SMILES C12C(NC(=O)N1)NC(=O)N2
Properties
Chemical formula	C4H6N4O2
Molar mass	142.12 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Glycoluril is an organic chemical composed of two cyclic urea groups joined across the same two-carbon chain. It is a white powder that has been used in water treatment, in paints and coatings, and occasionally as a slow-release fertilizer, and also occurs as the most prevalent impurity in commercial allantoin supplies.^[1] Glycouril itself and derivatives of it are used as monomers for producing the macrocyclic cucurbiturils polymers, which serve as hosts to bind to various neutral and anionic species. They are also used in several classes of non-cyclic structures that also bind a variety of structures.^[2][3]

Glycoluril can be synthesized by reacting two equivalents of urea with glyoxal. Likewise, using other vicinal carbonyl (or carbonyl hydrate) reactants give derivatives having various functional groups in place of the hydrogen atoms on the carbon chain.

References

1. "Summary of Data for Chemical Selection" (PDF). National Toxicology Program. Retrieved 2014-10-09.
2. Sijbesma, R. P.; Kentgens, A. P. M.; Lutz, E. T. G.; van der Maas, J. H.; Nolte, R. J. M. (1993). "Binding features of molecular clips derived from diphenylglycoluril". J. Am. Chem. Soc. 115 (20): 8999–9005. doi:10.1021/ja00073a015.
3. Branda, Neil; Grotzfeld, Robert M.; Valdes, Carlos; Rebek, Julius, Jr. (1995). "Control of Self-Assembly and Reversible Encapsulation of Xenon in a Self-Assembling Dimer by Acid-Base Chemistry". J. Am. Chem. Soc. 117 (1): 85–88. doi:10.1021/ja00106a010.