BCDMH

1-Bromo-3-chloro-5,5-dimethylhydantoin (BCDMH or bromochlorodimethylhydantoin) 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
Names
IUPAC name
1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione
Other names
bromochloro-5,5-dimethylhydantoin, BCDMH, agribrom, aquabrom, aquabrome, bromicide, bromochlorodimethylhydantoin, di-halo, halogene T30, nylate, photobrome, slimicide 78P
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.334
EC Number
  • 204-766-9
UNII
Properties
C5H6BrClN2O2
Molar mass 241.47 g/mol
Appearance White solid
Density 1.9 g/cm3
Melting point 159 to 163 °C (318 to 325 °F; 432 to 436 K)
0.15 g/100 ml (25 °C)
Hazards
Main hazards Flamability, Inhalation
Safety data sheet External MSDS
GHS pictograms
GHS Signal word Danger
H272, H302, H312, H314, H317, H332, H400
P210, P220, P221, P260, P261, P264, P270, P271, P272, P273, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, P363
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point Decomposes at 160°C
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

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 for recreational water sanitation and drinking water purification.[1] BCDMH works in the following manner:[2]

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:[3]

References
  1. NSF International (2012). "NSF/ANSI 60 - Drinking Water Treatment Chemicals - Health Effects". NSF Product and Service Listings. NSF International. Retrieved November 14, 2018. Bromochlorodimethylhydantoin[CL] - Bromicide Tablets - Algicide - Disinfection & Oxidation. [CL] The residual levels of chlorine (hypochlorite ion and hypochlorous acid), chlorine dioxide, chlorate ion, monochloramine and disinfection by-products shall be monitored in the finished drinking water to ensure compliance to all applicable regulations.
  2. South Australian Health Commission, "Standard for the Operation of Swimming Pools and Spa Pools in South Australia", Supplement C: Bromine Disinfection Archived 2009-05-21 at the Library of Congress Web Archives, page 8. Retrieved on 2009-05-12.
  3. Yasukazu Ura, Gozyo Sakata. "Chloroamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553.
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