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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-03-07 21:35:52 UTC
Update Date2022-03-07 03:17:38 UTC
HMDB IDHMDB0059903
Secondary Accession Numbers
  • HMDB59903
Metabolite Identification
Common NameDibromochloromethane
DescriptionDibromochloromethane, also known as chlorodibromomethane, belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. Dibromochloromethane is possibly neutral. Dibromochloromethane is a potentially toxic compound. In humans and laboratory animals, dibromochloromethane (and bromoform) are generally absorbed quickly. If required provide artificial respiration. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. Dibromochloromethane (and bromoform) are thought to be metabolized by at least two route-independent pathways: oxidation by cytochrome P-450 mixed function oxidase system and conjugation via glutathione S-transferase. Some studies in animals indicate that exposure to high doses of dibromochloromethane may also lead to liver and the kidney injury within a short period of time. Exposure to dibromochloromethane leads to central nervous system depression, which is probably the chief cause of death in acute exposures. Dibromochloromethane is oxidized into trihalomethanol by the cytochrome P-450 mixed function oxidase system of liver. After ingestion, excretion occurs primarily by exhalation of the compound or of CO2. Trihalomethanol then decomposes by loss of hydrogen and halide ions to yield the dihalocarbonyl (an analogue of phosgene), which is a highly reactive molecule, and may undergo a number of reactions, including direct reaction with cellular nucleophiles to yield covalent adducts, reaction with two moles of glutathione (GSH) to yield CO and oxidized glutathione (GSSG), and hydrolysis to yield CO2. Rinse mouth with water (never give anything by mouth to an unconscious person). EYES: irrigate opened eyes for several minutes under running water. Seek immediate medical advice.
Structure
Data?1563865989
Synonyms
ValueSource
ChlorodibromomethaneHMDB
Dibromo(chloro)methaneHMDB
Dibromo-chloro-methaneHMDB
DibromochloromethaneKEGG
Chemical FormulaCHBr2Cl
Average Molecular Weight208.28
Monoisotopic Molecular Weight205.813353033
IUPAC Namedibromo(chloro)methane
Traditional Namedibromochloromethane
CAS Registry NumberNot Available
SMILES
ClC(Br)Br
InChI Identifier
InChI=1S/CHBr2Cl/c2-1(3)4/h1H
InChI KeyGATVIKZLVQHOMN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentTrihalomethanes
Alternative Parents
Substituents
  • Trihalomethane
  • Hydrocarbon derivative
  • Organochloride
  • Organobromide
  • Alkyl chloride
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.76 g/LALOGPS
logP2.17ALOGPS
logP2.13ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.98 m³·mol⁻¹ChemAxon
Polarizability10.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+122.25830932474
DeepCCS[M-H]-120.36230932474
DeepCCS[M-2H]-155.79230932474
DeepCCS[M+Na]+129.97830932474
AllCCS[M+H]+133.932859911
AllCCS[M+H-H2O]+130.332859911
AllCCS[M+NH4]+137.232859911
AllCCS[M+Na]+138.232859911
AllCCS[M-H]-186.432859911
AllCCS[M+Na-2H]-193.332859911
AllCCS[M+HCOO]-200.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DibromochloromethaneClC(Br)Br1275.1Standard polar33892256
DibromochloromethaneClC(Br)Br770.4Standard non polar33892256
DibromochloromethaneClC(Br)Br798.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dibromochloromethane EI-B (Non-derivatized)splash10-004i-5900000000-0a5bd838330dc26d5a352017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibromochloromethane EI-B (Non-derivatized)splash10-004i-5900000000-0a5bd838330dc26d5a352018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dibromochloromethane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adi-0960000000-88b94675ee64d5a1fa392017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dibromochloromethane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-3900000000-2bd815439d7061bd9aa22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Positive-QTOFsplash10-0a4i-0090000000-331858b80ef37cc92b572016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Positive-QTOFsplash10-0a4i-0090000000-331858b80ef37cc92b572016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Positive-QTOFsplash10-0a4i-0090000000-331858b80ef37cc92b572016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Negative-QTOFsplash10-0udi-0090000000-23f04d542b2a35b2e3022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Negative-QTOFsplash10-0udi-0090000000-23f04d542b2a35b2e3022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Negative-QTOFsplash10-0udi-0090000000-23f04d542b2a35b2e3022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Positive-QTOFsplash10-0a4i-0090000000-262798c8821c1a784f9f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Positive-QTOFsplash10-0a4i-0090000000-262798c8821c1a784f9f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Positive-QTOFsplash10-00b9-0900000000-30e20910a1b4ef59649f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Negative-QTOFsplash10-0udi-0090000000-1cd0365290e6754179c72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Negative-QTOFsplash10-0udi-0090000000-1cd0365290e6754179c72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Negative-QTOFsplash10-0udi-0090000000-1cd0365290e6754179c72021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID29036
KEGG Compound IDC14692
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibromochloromethane
METLIN IDNot Available
PubChem Compound31296
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Weaver WA, Li J, Wen Y, Johnston J, Blatchley MR, Blatchley ER 3rd: Volatile disinfection by-product analysis from chlorinated indoor swimming pools. Water Res. 2009 Jul;43(13):3308-18. doi: 10.1016/j.watres.2009.04.035. Epub 2009 May 3. [PubMed:19501873 ]
  2. Aguilera-Herrador E, Lucena R, Cardenas S, Valcarcel M: Determination of trihalomethanes in waters by ionic liquid-based single drop microextraction/gas chromatographic/mass spectrometry. J Chromatogr A. 2008 Oct 31;1209(1-2):76-82. doi: 10.1016/j.chroma.2008.09.030. Epub 2008 Sep 13. [PubMed:18817919 ]
  3. Panyakapo M, Soontornchai S, Paopuree P: Cancer risk assessment from exposure to trihalomethanes in tap water and swimming pool water. J Environ Sci (China). 2008;20(3):372-8. [PubMed:18595407 ]
  4. Chowdhury S, Champagne P, James McLellan P: Investigating effects of bromide ions on trihalomethanes and developing model for predicting bromodichloromethane in drinking water. Water Res. 2010 Apr;44(7):2349-59. doi: 10.1016/j.watres.2009.12.042. Epub 2010 Jan 6. [PubMed:20080279 ]
  5. Padhi RK, Sowmya M, Mohanty AK, Bramha SN, Satpathy KK: Formation and speciation characteristics of brominated trihalomethanes in seawater chlorination. Water Environ Res. 2012 Nov;84(11):2003-9. [PubMed:23356015 ]
  6. Ye B, Wang W, Yang L, Wei J, E X: Formation and modeling of disinfection by-products in drinking water of six cities in China. J Environ Monit. 2011 May;13(5):1271-5. doi: 10.1039/c0em00795a. Epub 2011 Mar 18. [PubMed:21416099 ]
  7. Carter JM, Moran MJ, Zogorski JS, Price CV: Factors associated with sources, transport, and fate of chloroform and three other trihalomethanes in untreated groundwater used for drinking water. Environ Sci Technol. 2012 Aug 7;46(15):8189-97. doi: 10.1021/es301839p. Epub 2012 Jul 25. [PubMed:22799526 ]
  8. Hansen KM, Zortea R, Piketty A, Vega SR, Andersen HR: Photolytic removal of DBPs by medium pressure UV in swimming pool water. Sci Total Environ. 2013 Jan 15;443:850-6. doi: 10.1016/j.scitotenv.2012.11.064. Epub 2012 Dec 14. [PubMed:23247288 ]
  9. Yamamoto K, Mori Y: Simulating distribution of trihalomethane in tap water in the area receiving a combination of advanced treated water and conventionally treated different source water: 1998, 1999 and 2002 data on Osaka Prefecture and its surrounding cities, Japan. Bull Environ Contam Toxicol. 2009 Nov;83(5):677-80. doi: 10.1007/s00128-009-9777-6. Epub 2009 May 28. [PubMed:19475326 ]
  10. Silva ZI, Rebelo MH, Silva MM, Alves AM, Cabral Mda C, Almeida AC, Aguiar FR, de Oliveira AL, Nogueira AC, Pinhal HR, Aguiar PM, Cardoso AS: Trihalomethanes in Lisbon indoor swimming pools: occurrence, determining factors, and health risk classification. J Toxicol Environ Health A. 2012;75(13-15):878-92. doi: 10.1080/15287394.2012.690706. [PubMed:22788374 ]
  11. Villanueva CM, Castano-Vinyals G, Moreno V, Carrasco-Turigas G, Aragones N, Boldo E, Ardanaz E, Toledo E, Altzibar JM, Zaldua I, Azpiroz L, Goni F, Tardon A, Molina AJ, Martin V, Lopez-Rojo C, Jimenez-Moleon JJ, Capelo R, Gomez-Acebo I, Peiro R, Ripoll M, Gracia-Lavedan E, Nieuwenhujsen MJ, Rantakokko P, Goslan EH, Pollan M, Kogevinas M: Concentrations and correlations of disinfection by-products in municipal drinking water from an exposure assessment perspective. Environ Res. 2012 Apr;114:1-11. doi: 10.1016/j.envres.2012.02.002. Epub 2012 Mar 20. [PubMed:22436294 ]
  12. Zhang L, Xu L, Zeng Q, Zhang SH, Xie H, Liu AL, Lu WQ: Comparison of DNA damage in human-derived hepatoma line (HepG2) exposed to the fifteen drinking water disinfection byproducts using the single cell gel electrophoresis assay. Mutat Res. 2012 Jan 24;741(1-2):89-94. doi: 10.1016/j.mrgentox.2011.11.004. Epub 2011 Nov 16. [PubMed:22108252 ]
  13. Silva LK, Backer LC, Ashley DL, Gordon SM, Brinkman MC, Nuckols JR, Wilkes CR, Blount BC: The influence of physicochemical properties on the internal dose of trihalomethanes in humans following a controlled showering exposure. J Expo Sci Environ Epidemiol. 2013 Jan-Feb;23(1):39-45. doi: 10.1038/jes.2012.80. Epub 2012 Jul 25. [PubMed:22829048 ]
  14. Cervera MI, Beltran J, Lopez FJ, Hernandez F: Determination of volatile organic compounds in water by headspace solid-phase microextraction gas chromatography coupled to tandem mass spectrometry with triple quadrupole analyzer. Anal Chim Acta. 2011 Oct 17;704(1-2):87-97. doi: 10.1016/j.aca.2011.08.012. Epub 2011 Aug 11. [PubMed:21907025 ]
  15. Jakubowska N, Henkelmann B, Schramm KW, Namiesnik J: Optimization of a novel procedure for determination of VOCs in water and human urine samples based on SBSE coupled with TD-GC-HRMS. J Chromatogr Sci. 2009 Sep;47(8):689-93. [PubMed:19772746 ]