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{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 401811545
| verifiedrevid = 439489418
| Name = BCDMH
| Name = BCDMH
| ImageFile = BCDMH 100g.jpg
| ImageFile = BCDMH.png
| ImageSize = 250px
| ImageSize = 180px
| ImageName = BCDMH
| ImageAlt = Skeletal formula of BCDMH
| ImageFile1 = BCDMH.png
| ImageFile1 = BCDMH-3D-balls.png
| ImageSize1 = 150px
| ImageSize1 = 180
| ImageName1 = BCDMH
| ImageAlt1 = Ball-and-stick model of BCDMH
| ImageFile2 = BCDMH 100g.jpg
⚫
| IUPACName = 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione
| ImageSize2 = 150px
⚫
| OtherNames = bromochloro-5,5-dimethylhydantoin, BCDMH, agribrom, aquabrom, aquabrome, bromicide, di-halo, halogene T30, nylate, photobrome, slimicide 78P
| ImageAlt2 = Laboratory sample of BCDMH
⚫
| Section1 = {{Chembox Identifiers
⚫
| PIN = 1-Bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione
⚫
| OtherNames = bromochloro-5,5-dimethylhydantoin, BCDMH, agribrom, aquabrom, aquabrome, bromicide, bromochlorodimethylhydantoin, di-halo, halogene T30, HarvestCide, nylate, photobrome, [[slimicide]] 78P
⚫
|Section1={{Chembox Identifiers
| InChI = 1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
| InChI = 1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
| InChIKey = PQRDTUFVDILINV-UHFFFAOYAT
| InChIKey = PQRDTUFVDILINV-UHFFFAOYAT
Line 18: Line 22:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PQRDTUFVDILINV-UHFFFAOYSA-N
| StdInChIKey = PQRDTUFVDILINV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 16079-88-2
| CASNo = 32718-18-6
| SMILES = O=C1N(Br)C(=O)N(Cl)C1(C)C
| SMILES = O=C1N(Br)C(=O)N(Cl)C1(C)C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=29069
| ChemSpiderID =29069
| EINECS = 204-766-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W18O2G87ND
| ChEMBL = 1895319
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>5</sub>H<sub>6</sub>BrClN<sub>2</sub>O<sub>2</sub>
| Formula = C<sub>5</sub>H<sub>6</sub>BrClN<sub>2</sub>O<sub>2</sub>
| MolarMass = 241.47 g/mol
| MolarMass = 241.47 g/mol
| Appearance = White solid
| Appearance = White solid
| Density = 1.9 g/cm<sup>3</sup>
| Density = 1.9 g/cm<sup>3</sup>
| Solubility = 0.15 g/100 ml (25 °C)
| Solubility = 0.15 g/100 ml (25 °C)
| MeltingPtC = 159 to 163
| MeltingPt = 159–163 °C
| BoilingPt =
| MeltingPt_notes =
| BoilingPt =
}}
}}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/BR/1-bromo-3-chloro-5,5-dimethyl-2,4-imidazolidinedione.html External MSDS]
| ExternalSDS = [http://physchem.ox.ac.uk/MSDS/BR/1-bromo-3-chloro-5,5-dimethyl-2,4-imidazolidinedione.html External MSDS]
| MainHazards = Flamability, Inhalation
| MainHazards = Flamability, Inhalation
| NFPA-H = 3
| NFPA-H = 3
| NFPA-R = 1
| NFPA-R = 1
| NFPA-F = 1
| NFPA-F = 1
| FlashPt = Decomposes at 160°C
| FlashPt = Decomposes at 160°C
| RSPhrases = {{S8}}, {{S17}}, {{S26}}, {{S36}}, {{S37}}, {{S39}}, {{S41}}, {{S45}}
| GHSPictograms = {{GHS03}}{{GHS05}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|272|302|312|314|317|332|400}}
| 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}}
}}
}}
}}
}}


'''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]].
'''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]] used for recreational water and drinking [[water purification]]. BCDMH works in the following manner<ref>South Australian Health Commission, "Standard for the Operation of Swimming Pools and Spa Pools in South Australia", [http://www.dh.sa.gov.au/pehs/publications/code-bromine.pdf Supplement C: Bromine Disinfection], page 8. Retrieved on 2009-05-12.</ref>:
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 [[Swimming pool sanitation#Chlorine and bromine methods|recreational water sanitation]] and drinking [[water purification]].<ref name=NSF>{{Cite web
| url = http://info.nsf.org/Certified/PwsChemicals/Listings.asp?=&ChemicalName=Bromochlorodimethylhydantoin
| title = NSF/ANSI 60 - Drinking Water Treatment Chemicals - Health Effects
| access-date = November 14, 2018
| author = NSF International
| author-link = NSF International
| year = 2012
| work = NSF Product and Service Listings
| publisher = [[NSF International]]
| quote = 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.}}</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", [http://www.dh.sa.gov.au/pehs/publications/code-bromine.pdf Supplement C: Bromine Disinfection] {{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>


The initial BCDMH reacts with water (R = Dimethylhydantoin):
The initial BCDMH reacts with water (R = Dimethylhydantoin):
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Hypobromous acid partially dissociates in water:
Hypobromous acid partially dissociates in water:


: HOBr → H<sup>+</sup> + OBr<sup>-</sup>
: HOBr → H<sup>+</sup> + OBr<sup>−</sup>


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


: HOBr + Live pathogens → Br<sup>-</sup> + Dead pathogens
: HOBr + Live pathogens → Br<sup>−</sup> + Dead pathogens


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


: Br<sup>-</sup> + HOCl → HOBr + Cl<sup>-</sup>
: Br<sup>−</sup> + HOCl → HOBr + Cl<sup>−</sup>


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


==Preparation==
==Preparation==
This compound is prepared by first brominating, then chlorinating 5,5-dimethylhydantoin:<ref>{{Ullmann | title = Chloroamines | Yasukazu Ura, Gozyo Sakata | doi = 10.1002/14356007.a06_553}}</ref>
This compound is prepared by first [[brominating]], then [[Chlorination reaction|chlorinating]] 5,5-dimethylhydantoin:<ref>{{Ullmann | title = Chloroamines | author = Yasukazu Ura, Gozyo Sakata | doi = 10.1002/14356007.a06_553}}</ref>
:[[File:File:Preparation of BCDMH.png|500px]]
:[[File:Preparation of BCDMH.png|505px]]


==References==
==References==
{{reflist}}
{{Reflist}}


== External links ==
== External links ==
* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=61828&loc=ec_rcs PubChem Public Chemical Database (nih.gov)]
* [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=61828&loc=ec_rcs PubChem Public Chemical Database (nih.gov)]
* [http://www.e1.greatlakes.com/common/msdspdf/00255.pdf External MSDS]
* [https://web.archive.org/web/20070928060017/http://www.e1.greatlakes.com/common/msdspdf/00255.pdf External MSDS]


[[Category:Disinfectants]]
[[Category:Disinfectants]]
Line 81: Line 102:
[[Category:Organochlorides]]
[[Category:Organochlorides]]
[[Category:Hydantoins]]
[[Category:Hydantoins]]

[[ja:1-ブロモ-3-クロロ-5,5-ジメチルヒダントイン]]
[[ru:1-бром-3-хлор-5,5-диметилгидантоин]]

Latest revision as of 22:21, 4 February 2024

BCDMH
Skeletal formula of BCDMH
Ball-and-stick model of BCDMH
Laboratory sample of 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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.334 Edit this at Wikidata
EC Number
  • 204-766-9
UNII
  • InChI=1S/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 checkY
    Key: PQRDTUFVDILINV-UHFFFAOYSA-N checkY
  • InChI=1/C5H6BrClN2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
    Key: PQRDTUFVDILINV-UHFFFAOYAT
  • O=C1N(Br)C(=O)N(Cl)C1(C)C
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
Occupational safety and health (OHS/OSH):
Main hazards
 Flamability, Inhalation
GHS labelling:
GHS03: OxidizingGHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H272, H302, H312, H314, H317, H332, H400
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)

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

[edit]

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

References

[edit]
  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.
[edit]
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