1-Bromo-3-chloro-5,5-dimethylhydantoin (CHEM001525)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2026-03-31 17:31:27 UTC
Accession NumberCHEM001525
Identification
Common Name1-Bromo-3-chloro-5,5-dimethylhydantoin
ClassSmall Molecule
Description1-Bromo-3-chloro-5,5-dimethylhydantoin (BCDMH) is an organobromide compound. It is 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 used as a solid halohydantion product for water disinfection and is an excellent source of both chlorine and bromine as it reacts slowly with water releasing hypochlorous acid and hypobromous acid along with 5,5-dimethylhydantion. It is primarily used as a chemical disinfectant for recreational water and drinking water purification. BCDMH was described as being responsible for an epidemic of irritant contact dermatitis in the UK (1983). It is prepared by first brominating, then chlorinating 5,5-dimethylhydantoin.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AquabromMeSH
Di-haloMeSH
BromicideMeSH
Chemical FormulaC5H6BrClN2O2
Average Molecular Mass241.470 g/mol
Monoisotopic Mass239.930 g/mol
CAS Registry Number16079-88-2
IUPAC Name1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione
Traditional Namebcdmh
SMILESCC1(C)N(Br)C(=O)N(Cl)C1=O
InChI IdentifierInChI=1S/C5H6BrClN2O2/c1-5(2)3(10)8(7)4(11)9(5)6/h1-2H3
InChI KeyPIEXCQIOSMOEOU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • Dicarboximide
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.71 g/LALOGPS
logP-0.96ALOGPS
logP1.23ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.52 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-d1df49a8979a0fc3c8a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0190000000-786a23e8da82f1b6cf29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9440000000-ea61f9077059e57cb4faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f7ee03be3bb07af7e0f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-961516cfeff08c632d66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0300-3900000000-bcb95dabfc5f65449754Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityBCDMH likely causes tissue irritation through its breakdown products (hypochlorous acid and hypobromous acid) which, on their own, can cause local irritation. 5,5-dimethylhydantoin is also produced spontaneously from BCDMH decomposition and hydantoins are also known to be allergens.
MetabolismSpontaneously reacts with water releasing hypochlorous acid and hypobromous acid along with 5,5-dimethylhydantion.
Toxicity ValuesLD50: 1390 mg/kg (Oral, Rat) (7) LD50: >2000 mg/kg (Dermal, Rabbit) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (4)
Uses/SourcesUsed as a solid halohydantion product for water disinfection in swimming pools. Occupational exposure to BCDMH may occur through inhalation and dermal contact with this compound at workplaces where BCDMH is produced or used.
Minimum Risk LevelNot Available
Health EffectsCorrosive. Acute exposure causes irreversible eye damage and skin burns. Eye contact may cause loss of vision. Irritating to nose and throat and may be fatal if large quantities are inhaled. Harmful if absorbed through skin or swallowed. Can cause contact dermatitis through exposure in swimming pools. It is not carcinogenic or mutagenic.
SymptomsIrritating to nose and throat. Can cause redness and itching of skin due to chronic skin exposure.
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID61828
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available