3-Bromo-1-chloro-5,5-dimethyl-2,4-imidazolidinedione

Abstract

[126-06-7] C5H6BrClN2O2 (MW: 241.47) InChI = 1S/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 InChIKey = PQRDTUFVDILINV-UHFFFAOYSA-N (oxidizing activator) Alternate Names: 3-bromo-1-chloro-5,5-dimethylhydantoin, 1-chloro-3-bromo-5,5-dimethylhydantoin, BCDMH. Physical Data: d 1.91 ± 0.1 g cm−3; mp 163–164 °C; active bromine 33% minimum, active chlorine 14% minimum. Solubility: soluble in benzene, methylene dichloride, chloroform. Solubility in water is 8.260 g L−1 at 25 °C. Form Supplied in: white powder with faint acrid odor; commercially available. Analysis of Reagent Purity: IR and NMR spectroscopy, X-ray diffraction; melting point analysis is useful for the determination of purity. Preparative Methods:2 sequential reaction of 5,5-dimethylhydantoin in aqueous alkaline medium with elementary bromine and chlorine, or mixing equal amounts of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) via halogen migration provides the title compound in high yield. The latter method provides a safe process, mitigating the need for bromine and chlorine (eqs 1 and 2). (1) (2) Purification: for most applications, it is not necessary to purify BCDMH. If purification is necessary, refer to the purification method of DCDMH or DBDMH.3 Handling, Storage, and Precautions: the title compound should be kept in a dry box to avoid decomposition due to exposure to water. Keep away from combustible materials. This compound is a severe eye and skin irritant. When handling it, wear suitable protective clothing, gloves, and eye/face protection. When heated to decomposition, hydrogen chloride, hydrogen bromide, and nitrogen oxide gases are formed. In case of fire and/or explosion, do not breathe fumes. 3-Bromo-1-chloro-5,5-dimethyl-2,4-imidazolidinedione is a convenient alternative of elementary halogen source, bearing two different, yet active, halogen atoms. 3-Bromo-1-chloro-5,5-dimethyl-2,4-imidazolidinedione is primarily applied as a germicide, fungicide, and disinfectant, but seldom in organic synthesis. Recently, BCDMH has found applications in transition metal-catalyzed reactions due to its mild oxidizing ability.