Hydantoin

Hydantoin
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
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)
Structure
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	?°C
R/S statement	R: ? S: 24/25
RTECS number	MT8210000
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	?
Spectral data	UV, IR, NMR, MS
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) Chemical infobox

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.

Synthesis

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."

Uses

Chemical

When hydantoin reacts with hot, dilute hydrochloric acid, glycine is one of the products.

Medicine

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).

Pharmaceutical Industry

Hydantoin is used to synthesize the following anticonvulsants:

References and end notes

Hydantoin - CAS 461-72-3 - Catalog of Chemical Suppliers ChemExper.com.

External links

Organic compounds

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