Hydantoin
From Wikipedia, the free encyclopedia
| Hydantoin | |
|---|---|
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| General | |
| Systematic name | imidazolidine-2,4-dione |
| Other names | glycolylurea, 2,4(3H,5H)-Imidazoledione |
| Molecular formula | C3H4N2O2 |
| SMILES | C1C(=O)NC(=O)N1 |
| InChI | InChI=1/C3H4N2O2/c6-2-1-4-3(7)5-2 /h1H2,(H2,4,5,6,7)/f/h4-5H |
| Molar mass | 100.076 g/mol |
| Appearance | White crystalline powder |
| CAS number | [461-72-3] [1] |
| Properties | |
| Density and phase | ? g/cm3, solid |
| Solubility in water | 39.7 g/L (100°C) |
| Other solvents | ? |
| Melting point | 220°C (493 K) |
| Boiling point | ?°C (? K) |
| Related compounds | |
| Related heterocyclic compounds |
imidazolidine (see imidazole), cyanuric acid |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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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 [1].
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[edit] Synthesis
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 [2] 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 abtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate [3]. According to the 1911 Encyclopedia Britannica, hydantoin can be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia."
[edit] Uses
[edit] Chemical
When hydantoin reacts with hot, dilute hydrochloric acid, glycine is one of the products.
[edit] Medicine
[edit] Derivatives
Dantrolene is used in malignant hyperthermia, neuroleptic malignant syndrome, spasticity, and Ecstasy intoxication.
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).
[edit] Pharmaceutical Industry
Hydantoin is used to synthesize the following anticonvulsants:
[edit] External links
- PubChem Compound Summary: Hydantoin
- Hazard DB: Hydantoin
- NIH ChemIDPlus: Hydantoin
- Hydantoin - CAS 461-72-3 - Catalog of Chemical Suppliers
ChemExper.com.
[edit] References
- ^ 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.
This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.
