5,5-Dimethylhydantoin

5,5-Dimethylhydantoin
Names
	IUPAC name 4,4-Dimethyl-2,5-dioxoimidazolidine
Identifiers
CAS Number	77-71-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:183672;
ChEMBL	ChEMBL3181806;
ChemSpider	6246;
ECHA InfoCard	100.000.957
EC Number	201-051-3;
PubChem CID	6491;
UNII	34032MQ9RO;
CompTox Dashboard (EPA)	DTXSID5021754 ;
	InChI InChI=1S/C5H8N2O2/c1-5(2)3(8)6-4(9)7-5/h1-2H3,(H2,6,7,8,9) Key: YIROYDNZEPTFOL-UHFFFAOYSA-N;
	SMILES CC1(C(=O)NC(=O)N1)C;
Properties
Chemical formula	C5H8N2O2
Molar mass	128.131 g·mol−1
Melting point	174–176 °C (345–349 °F; 447–449 K)
Solubility	very soluble in ethanol, ether, acetone, benzene, chloroformsoluble in DMSO
log P	-0.48
Vapor pressure	0.0000028 mmHg
Acidity (pKa)	9.19
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5,5-Dimethylhydantoin (DMH, systematic name 4,4-dimethyl-2,5-dioxoimidazolidine) is a derivative of hydantoin having two methyl groups as substituents on the ring carbon. DMH can be used in silver electroplating baths as an alternative to cyanide.^[1] It is a degradation product of 1,3-dibromo-5,5-dimethylhydantoin that can be detected on foods that have not been properly washed.^[2] It can be easily produced by a Bucherer–Bergs reaction, warming a mixture of acetone cyanohydrin and ammonium carbonate.^[3]

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Reaction of DMH with various halogens gives N,N′-dihalo derivatives, such as diido-5,5-dimethylhydantoin [de],^[4]^[5] bromochloro-5,5-dimethylhydantoin,^[6] and dibromo-5,5-dimethylhydantoin, which can be used as reagents to supply of electrophilic halogen atoms or hypohalous acids (or synthetic equivalents of them). Sodium 4,4-dimethyl-2,5-dioxoimidazolidin-1-ide, the sodium salt of its conjugate base, has been commercialized as a stabilizer for active chlorine in the papermaking industry.^[7]

See also