DBDMH

1,3-Dibromo-5,5-Dimethylhydantoin
Skeletal formula of DBDMH	Ball-and-stick model of the DBDMH molecule
Names
	IUPAC name 1,3-Dibromo-5,5-dimethylhydantoin
	Other names DBDMH, Dibromantin, Dibromodimethylhydantoin
Identifiers
CAS Number	77-48-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3184055;
ChemSpider	6234 ;
ECHA InfoCard	100.000.938
EC Number	201-030-9;
PubChem CID	6479;
UNII	V9R5F9I7MZ ;
CompTox Dashboard (EPA)	DTXSID3035341 ;
	InChI InChI=1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 Key: VRLDVERQJMEPIF-UHFFFAOYSA-N ; InChI=1/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 Key: VRLDVERQJMEPIF-UHFFFAOYAQ;
	SMILES O=C1N(Br)C(=O)N(Br)C1(C)C;
Properties
Chemical formula	C5H6Br2N2O2
Molar mass	285.923 g·mol−1
Appearance	White solid
Density	1.36 g/cm3
Melting point	197 to 203 °C (387 to 397 °F; 470 to 476 K)
Solubility in water	0.1 g/100 mL (20 °C)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H302, H314, H317, H319, H400, H410
GHS precautionary statements	P260, P261, P264, P270, P272, P273, P280, P301+310, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P321, P330, P333+313, P337+313, P363, P391, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

DBDMH (also known as 1,3-Dibromo-5,5-Dimethylhydantoin) is an organic compound derived from the heterocycle called dimethylhydantoin. This white crystalline compound with a slight bromine odor is widely used as a disinfectant used for drinking water purification, recreational water treatment, as a bleaching agent in pulp and paper mills, and for treating industrial/commercial water cooling systems. [1] Its action does not involve the use of hypochlorous acid.

Mechanism of action

1,3-Dibromo-5,5-Dimethylhydantoin is a source of bromine, which is equivalent to hypobromous acid (HOBr).

Br₂X + 2 H₂O → 2 HOBr + H₂X

(Where H₂X is 5,5-dimethylhydantoin)

With a pK_a of 8.6, hypobromous acid partially dissociates in water:

HOBr ⇌ H⁺ + BrO⁻

Hypobromous acid serves as a source of "Br⁺," which produces bromide ions in the process of disinfection:

HOBr + live pathogens → Br⁻ + dead pathogens

The resulting bromide ions can then undergo oxidation to hypobromous acid in the presence of an oxidizer of sufficient strength e.g. ozone, hypochlorous acid, potassium monopersulfate. This reoxidation process is commonly called "activation" of the bromide ion:

Br⁻ + HOCl → HOBr + Cl⁻

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References

David Ioffe, Arieh Kampf "Bromine, Organic Compounds" in Kirk-Othmer Encyclopedia of Chemical Technology, 2002, by John Wiley & Sons. doi: 10.1002/0471238961.0218151325150606.a01

External links

MSDS

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[1] David Ioffe, Arieh Kampf "Bromine, Organic Compounds" in Kirk-Othmer Encyclopedia of Chemical Technology, 2002, by John Wiley & Sons. doi: 10.1002/0471238961.0218151325150606.a01