3D model (JSmol)
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|Except where noted otherwise, data are given for|
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound which can be thought of as a cyclic "double-condensation reaction" product of glycolic acid and urea. Its chemical structure, shown in the Table of Properties at right, is similar to imidazolidine except that the molecule has carbonyl groups in the number 2 and 4 positions in the ring. Imidazolidine is the hydrogen-saturated analogue of imidazole. Imidazole is a heterocyclic aromatic organic compound.
In a more general sense, hydantoins can refer to chemical compounds which have substituent groups bonded to a hydantoin ring "skeletal structure". For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.
Hydantoin was first isolated in 1881 by Adolf von Baeyer in the course of his study of uric acid. He obtained it by hydrogenation of Allantoin hence the name. Urech in 1873  synthesized the derivative 5-methylhydantoin from alanine sulfate and potassium cyanate in what is now known as the Urech hydantoin synthesis:
The 5,5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate.. This reaction type is called the Bucherer-Bergs reaction  .
Halogenated analogues of hydantoin are used as chlorinating or brominating agents in disinfectant/sanitizer or biocide products. The three major halogenated derivatives are dichlorodimethylhydantoin (DCDMH), bromochlorodimethylhydantoin (BCDMH), and dibromodimethylhydantoin (DBDMH).
Hydantoin is used to synthesize the following anticonvulsants:
- PubChem Compound Summary: Hydantoin
- Hazard DB: Hydantoin
- NIH ChemIDPlus: Hydantoin
- Hydantoin - CAS 461-72-3 - Catalog of Chemical Suppliers
- The Chemistry of the Hydantoins.Elinor Ware Chem. Rev.; 1950; 46(3) pp 403 - 470; doi:10.1021/cr60145a001
- Urech, Ann., 165, 99 (1873).
- Organic Syntheses, Coll. Vol. 3, p.323 (1955); Vol. 20, p.42 (1940) Link.
- Bucherer and Steiner, J. prakt. Chem., 140, 291 (1934).
- Bergs, Ger. pat. 566,094 (1929) [C. A., 27, 1001 (1933)].