BCDMH

BCDMH
Names
	Preferred 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, HarvestCide, nylate, photobrome, slimicide 78P
Identifiers
CAS Number	32718-18-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1895319;
ChemSpider	29069 ;
ECHA InfoCard	100.004.334
EC Number	204-766-9;
PubChem CID	31335;
UNII	W18O2G87ND ;
CompTox Dashboard (EPA)	DTXSID7029162 ;
	InChI InChI=1S/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 Key: PQRDTUFVDILINV-UHFFFAOYSA-N ; InChI=1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 Key: PQRDTUFVDILINV-UHFFFAOYAT;
	SMILES O=C1N(Br)C(=O)N(Cl)C1(C)C;
Properties
Chemical formula	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)
Solubility in water	0.15 g/100 ml (25 °C)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flamability, Inhalation
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H272, H302, H312, H314, H317, H332, H400
Precautionary statements	P210, P220, P221, P260, P261, P264, P270, P271, P272, P273, P280, P301 P312, P301 P330 P331, P302 P352, P303 P361 P353, P304 P312, P304 P340, P305 P351 P338, P310, P312, P321, P322, P330, P333 P313, P363, P370 P378, P391, P405, P501
NFPA 704 (fire diamond)	3 1 1
Flash point	Decomposes at 160°C
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 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; the hypochlorous acid itself act directly as a disinfectant in the process.

Preparation

This compound is prepared by first brominating, then chlorinating 5,5-dimethylhydantoin:^[3]

References

^ 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.
^ 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.
^ Yasukazu Ura, Gozyo Sakata. "Chloroamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553. ISBN 978-3527306732.

External links

[NSF-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. ISBN 978-3527306732.

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