BCDMH

BCDMH
IUPAC name 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione
Other names bromochloro-5,5-dimethylhydantoin, BCDMH, agribrom, aquabrom, aquabrome, bromicide, di-halo, halogene T30, nylate, photobrome, slimicide 78P
Identifiers
CAS number	16079-88-2 Y
PubChem	31335
ChemSpider	29069 Y
Jmol-3D images	Image 1
SMILES O=C1N(Br)C(=O)N(Cl)C1(C)C
InChI InChI=1S/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 Y Key: PQRDTUFVDILINV-UHFFFAOYSA-N Y InChI=1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 Key: PQRDTUFVDILINV-UHFFFAOYAT
Properties
Molecular formula	C5H6BrClN2O2
Molar mass	241.47 g/mol
Appearance	White solid
Density	1.9 g/cm3
Melting point	159–163 °C
Solubility in water	0.15 g/100 ml (25 °C)
Hazards
MSDS	External MSDS
R/S statement	S8, S17, S26, S36, S37, S39, S41, S45
Main hazards	Flamability, Inhalation
NFPA 704	1 3 1
Flash point	Decomposes at 160°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1-Bromo-3-chloro-5,5-dimethylhydantoin (BCDMH) is a chemical structurally related to hydantoin. It is a white crystalline compound with a slight bromine and acetone odor and is insoluble in water, but soluble in acetone.

BCDMH is an excellent source of both chlorine and bromine as it reacts slowly with water releasing hypochlorous acid and hypobromous acid. It used as a chemical disinfectant used for recreational water and drinking water purification. BCDMH works in the following manner:^[1]

The initial BCDMH reacts with water (R = Dimethylhydantoin):

BrClR + 2 H₂O → HOBr + HOCl + RH₂

Hypobromous acid partially dissociates in water:

HOBr → H⁺ + OBr^-

Hypobromous acid oxidizes the substrate, itself being reduced to bromide:

HOBr + Live pathogens → Br^- + Dead pathogens

The bromide ions are oxidized with the hypochlorous acid that was formed from the initial BCDMH:

Br^- + HOCl → HOBr + Cl^-

This produces more hypobromous acid. However, the hypochlorous acid itself does act directly as a disinfectant in the process.

Preparation

This compound is prepared by first brominating, then chlorinating 5,5-dimethylhydantoin:^[2]

References

1. ^ South Australian Health Commission, "Standard for the Operation of Swimming Pools and Spa Pools in South Australia", Supplement C: Bromine Disinfection, page 8. Retrieved on 2009-05-12.
2. ^ Yasukazu Ura, Gozyo Sakata (2005), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_553 

External links

• PubChem Public Chemical Database (nih.gov)
• External MSDS