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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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]
Reaction of DMH with various halogens gives N,N′-dihalo derivatives, such as diido-5,5-dimethylhydantoin , [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]
