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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 401811545 |
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| verifiedrevid = 439489418 |
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| Name = BCDMH |
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| Name = BCDMH |
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| ImageFile1 = BCDMH 100g.jpg |
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| ImageSize1 = 150px |
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| ImageName1 = BCDMH |
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| ImageFile = BCDMH.png |
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| ImageFile = BCDMH.png |
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| ImageSize = 180px |
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| ImageSize = 180px |
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| ImageName = BCDMH |
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| ImageAlt = Skeletal formula of BCDMH |
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| ImageFile1 = BCDMH-3D-balls.png |
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| IUPACName = 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione |
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| ImageSize1 = 180 |
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| OtherNames = bromochloro-5,5-dimethylhydantoin, BCDMH, agribrom, aquabrom, aquabrome, bromicide, di-halo, halogene T30, nylate, photobrome, slimicide 78P |
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| ImageAlt1 = Ball-and-stick model of BCDMH |
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| Section1 = {{Chembox Identifiers |
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| ImageFile2 = BCDMH 100g.jpg |
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| ImageSize2 = 150px |
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| ImageAlt2 = Laboratory sample of BCDMH |
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| PIN = 1-Bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione |
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| OtherNames = bromochloro-5,5-dimethylhydantoin, BCDMH, agribrom, aquabrom, aquabrome, bromicide, bromochlorodimethylhydantoin, di-halo, halogene T30, HarvestCide, nylate, photobrome, ] 78P |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 |
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| InChI = 1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 |
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| InChIKey = PQRDTUFVDILINV-UHFFFAOYAT |
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| InChIKey = PQRDTUFVDILINV-UHFFFAOYAT |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PQRDTUFVDILINV-UHFFFAOYSA-N |
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| StdInChIKey = PQRDTUFVDILINV-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 16079-88-2 |
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| CASNo = 32718-18-6 |
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| SMILES = O=C1N(Br)C(=O)N(Cl)C1(C)C |
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| SMILES = O=C1N(Br)C(=O)N(Cl)C1(C)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=29069 |
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| ChemSpiderID =29069 |
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| EINECS = 204-766-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = W18O2G87ND |
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| ChEMBL = 1895319 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>5</sub>H<sub>6</sub>BrClN<sub>2</sub>O<sub>2</sub> |
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| Formula = C<sub>5</sub>H<sub>6</sub>BrClN<sub>2</sub>O<sub>2</sub> |
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| MolarMass = 241.47 g/mol |
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| MolarMass = 241.47 g/mol |
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| Appearance = White solid |
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| Appearance = White solid |
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| Density = 1.9 g/cm<sup>3</sup> |
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| Density = 1.9 g/cm<sup>3</sup> |
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| Solubility = 0.15 g/100 ml (25 °C) |
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| Solubility = 0.15 g/100 ml (25 °C) |
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| MeltingPtC = 159 to 163 |
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| MeltingPt = 159–163 °C |
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| BoilingPt = |
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| MeltingPt_notes = |
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| BoilingPt = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = Flamability, Inhalation |
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| MainHazards = Flamability, Inhalation |
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| NFPA-H = 3 |
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| NFPA-H = 3 |
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| NFPA-R = 1 |
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| NFPA-R = 1 |
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| NFPA-F = 1 |
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| NFPA-F = 1 |
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| FlashPt = Decomposes at 160°C |
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| FlashPt = Decomposes at 160°C |
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| RSPhrases = {{S8}}, {{S17}}, {{S26}}, {{S36}}, {{S37}}, {{S39}}, {{S41}}, {{S45}} |
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| GHSPictograms = {{GHS03}}{{GHS05}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|272|302|312|314|317|332|400}} |
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| PPhrases = {{P-phrases|210|220|221|260|261|264|270|271|272|273|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|330|333+313|363|370+378|391|405|501}} |
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'''1-Bromo-3-chloro-5,5-dimethylhydantoin''' ('''BCDMH''') is a chemical structurally related to ]. It is a white crystalline compound with a slight ] and ] odor and is insoluble in water, but soluble in ]. |
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'''1-Bromo-3-chloro-5,5-dimethylhydantoin''' ('''BCDMH''' or '''bromochlorodimethylhydantoin''') is a chemical structurally related to ]. It is a white crystalline compound with a slight ] and ] odor and is insoluble in water, but soluble in ]. |
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BCDMH is an excellent source of both chlorine and bromine as it reacts slowly with water releasing ] and ]. It used as a chemical ] used for recreational water and drinking ]. BCDMH works in the following manner:<ref>South Australian Health Commission, "Standard for the Operation of Swimming Pools and Spa Pools in South Australia", , page 8. Retrieved on 2009-05-12.</ref> |
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BCDMH is an excellent source of both ] and ] as it reacts slowly with water releasing ] and ]. It used as a chemical ] for ] and drinking ].<ref name=NSF>{{Cite web |
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| url = http://info.nsf.org/Certified/PwsChemicals/Listings.asp?=&ChemicalName=Bromochlorodimethylhydantoin |
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| title = NSF/ANSI 60 - Drinking Water Treatment Chemicals - Health Effects |
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| access-date = November 14, 2018 |
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| author = NSF International |
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| author-link = NSF International |
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| year = 2012 |
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| work = NSF Product and Service Listings |
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| publisher = ] |
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| quote = Bromochlorodimethylhydantoin - Bromicide Tablets - Algicide - Disinfection & Oxidation. The residual levels of chlorine (] ion and ]), ], chlorate ion, ] and disinfection by-products shall be monitored in the finished drinking water to ensure compliance to all applicable regulations.}}</ref> BCDMH works in the following manner:<ref>South Australian Health Commission, "Standard for the Operation of Swimming Pools and Spa Pools in South Australia", {{Webarchive|url=http://webarchive.loc.gov/all/20090521114852/http://www.dh.sa.gov.au/pehs/publications/code-bromine.pdf |date=2009-05-21 }}, page 8. Retrieved on 2009-05-12.</ref> |
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The initial BCDMH reacts with water (R = Dimethylhydantoin): |
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The initial BCDMH reacts with water (R = Dimethylhydantoin): |
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Hypobromous acid partially dissociates in water: |
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Hypobromous acid partially dissociates in water: |
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: HOBr → H<sup>+</sup> + OBr<sup>-</sup> |
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: HOBr → H<sup>+</sup> + OBr<sup>−</sup> |
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Hypobromous acid oxidizes the substrate, itself being reduced to bromide: |
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Hypobromous acid oxidizes the substrate, itself being reduced to bromide: |
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: HOBr + Live pathogens → Br<sup>-</sup> + Dead pathogens |
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: HOBr + Live pathogens → Br<sup>−</sup> + Dead pathogens |
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The bromide ions are oxidized with the hypochlorous acid that was formed from the initial BCDMH: |
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The bromide ions are oxidized with the hypochlorous acid that was formed from the initial BCDMH: |
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: Br<sup>-</sup> + HOCl → HOBr + Cl<sup>-</sup> |
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: Br<sup>−</sup> + HOCl → HOBr + Cl<sup>−</sup> |
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This produces more hypobromous acid. However, the hypochlorous acid itself does act directly as a disinfectant in the process. |
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This produces more hypobromous acid; the hypochlorous acid itself act directly as a disinfectant in the process. |
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==Preparation== |
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==Preparation== |
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This compound is prepared by first brominating, then chlorinating 5,5-dimethylhydantoin:<ref>{{Ullmann | title = Chloroamines | author = Yasukazu Ura, Gozyo Sakata | doi = 10.1002/14356007.a06_553}}</ref> |
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This compound is prepared by first ], then ] 5,5-dimethylhydantoin:<ref>{{Ullmann | title = Chloroamines | author = Yasukazu Ura, Gozyo Sakata | doi = 10.1002/14356007.a06_553}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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== External links == |
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== External links == |
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