DBDMH: Difference between revisions
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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey. |
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{{chembox |
{{chembox |
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| Verifiedimages = changed |
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| Name = DBDMH |
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| Watchedfields = changed |
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| verifiedrevid = 399740402 |
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| ImageSize = 150px |
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| ImageName = DBDMH |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL1 = 120px |
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| ImageAltL1 = Skeletal formula of DBDMH |
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| ImageFileR1 = DBDMH 3D ball.png |
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| ImageSizeR1 = 130 |
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| ImageAltR1 = Ball-and-stick model of the DBDMH molecule |
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| PIN = 1,3-Dibromo-5,5-dimethylimidazolidine-2,4-dione |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 |
| InChI = 1/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 |
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| InChIKey = VRLDVERQJMEPIF-UHFFFAOYAQ |
| InChIKey = VRLDVERQJMEPIF-UHFFFAOYAQ |
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| SMILES = O=C1N(Br)C(=O)N(Br)C1(C)C |
| SMILES = O=C1N(Br)C(=O)N(Br)C1(C)C |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = V9R5F9I7MZ |
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| PubChem = 6479 |
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| EC_number = 201-030-9 |
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| ChEMBL = 3184055 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 |
| StdInChI = 1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VRLDVERQJMEPIF-UHFFFAOYSA-N |
| StdInChIKey = VRLDVERQJMEPIF-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 77-48-5 |
| CASNo = 77-48-5 |
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}} |
}} |
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|Section2={{Chembox Properties |
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| C =5|H=6|Br=2|N=2|O=2 |
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| Appearance = White solid |
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| Density = 1.36 g/cm<sup>3</sup> |
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| Solubility = 0.1 g/100 mL (20 °C) |
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| MeltingPtC = 197 to 203 |
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| MeltingPt_notes = |
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| BoilingPt = |
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| ExternalMSDS = |
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| ExternalSDS = |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|302|314|317|319|410}} |
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| PPhrases = {{P-phrases|260|261|264|270|272|273|280|301+310|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|321|330|333+313|337+313|363|391|405|501}} |
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'''DBDMH''' is an organic compound derived from the [[heterocycle]] called dimethyl[[hydantoin]]. 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. <ref>David Ioffe, Arieh Kampf |
'''DBDMH''' (also known as '''1,3-Dibromo-5,5-Dimethylhydantoin''') is an organic compound derived from the [[heterocycle]] called dimethyl[[hydantoin]]. 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. <ref>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}}</ref> Its action does not involve the use of [[hypochlorous acid]]. |
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==Mechanism of action== |
==Mechanism of action== |
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1,3-Dibromo-5,5-Dimethylhydantoin is a source of bromine, which is equivalent to hypobromous acid (HOBr). |
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:Br<sub>2</sub>X + 2 H<sub>2</sub>O → 2 HOBr + H<sub>2</sub>X |
:Br<sub>2</sub>X + 2 H<sub>2</sub>O → 2 HOBr + H<sub>2</sub>X |
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(Where H<sub>2</sub>X is 5,5-dimethylhydantoin) |
(Where H<sub>2</sub>X is 5,5-dimethylhydantoin) |
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With a |
With a [[pKa|p''K''<sub>a</sub>]] of 8.6, hypobromous acid partially dissociates in water: |
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:HOBr |
:HOBr ⇌ H<sup>+</sup> + BrO<sup>−</sup> |
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Hypobromous acid serves as a source of "Br<sup>+</sup>," which produces bromide ions in the process of disinfection: |
Hypobromous acid serves as a source of "Br<sup>+</sup>," which produces bromide ions in the process of disinfection: |
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:HOBr + live pathogens → Br<sup> |
:HOBr + live pathogens → Br<sup>−</sup> + dead pathogens |
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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 mono[[persulfate]]. This reoxidation process is commonly called "activation" of the bromide ion: |
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 mono[[persulfate]]. This reoxidation process is commonly called "activation" of the bromide ion: |
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:Br<sup> |
:Br<sup>−</sup> + HOCl → HOBr + Cl<sup>−</sup> |
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==References== |
==References== |
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==External links== |
==External links== |
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* [http://www.sigmaaldrich.com/MSDS/MSDS/PleaseWaitMSDSPage.do?language=&country=IE&brand=ALDRICH&productNumber=157902&PageToGoToURL=http://www.sigmaaldrich.com/catalog/product/aldrich/157902?lang=en®ion=IE MSDS] |
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* [http://chemada.com/cat1/items/DBDMH.pdf MSDS] |
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[[Category:Organobromides]] |
[[Category:Organobromides]] |
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[[Category:Hydantoins]] |
[[Category:Hydantoins]] |
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[[ja:1,3-ジブロモ-5,5-ジメチルヒダントイン]] |
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[[ru:1,3-дибром-5,5-диметилгидантоин]] |
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