Dibromomethane (T3D1795)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-06-22 16:08:37 UTC
Update Date2014-12-24 20:24:39 UTC
Accession NumberT3D1795
Identification
Common NameDibromomethane
ClassSmall Molecule
DescriptionDibromomethane is an organobromide compound. It may be produced synthetically or naturally by marine algae. Dibromomethane is used as a solvent, gage fluid and in organic synthesis. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (4, 7)
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
CH2Br2
Dibrommethan
Dibromoethane
Dibromomethylene
Methylenbromid
Methylene bromide
methylene bromide ion (1+)
methylene bromide, 79Br2-labeled
methylene bromide, 80Br-labeled
methylene bromide, 80Br2-labeled
methylene bromide, 82Br-labeled
methylene bromide, 82Br2-labeled
Methylene dibromide
Qmacd\qih
Chemical FormulaCH2Br2
Average Molecular Mass173.835 g/mol
Monoisotopic Mass171.852 g/mol
CAS Registry Number74-95-3
IUPAC Namedibromomethane
Traditional Namedibromomethane
SMILESBrCBr
InChI IdentifierInChI=1S/CH2Br2/c2-1-3/h1H2
InChI KeyInChIKey=FJBFPHVGVWTDIP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as halomethanes. These are organic compounds in which at least one of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentHalomethanes
Alternative Parents
Substituents
  • Halomethane
  • Hydrocarbon derivative
  • Organobromide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless to pale yellow liquid.
Experimental Properties
PropertyValue
Melting Point-52.5°C
Boiling PointNot Available
Solubility11.9 mg/mL at 30°C [GROSS,PM & SAYLOR,JH (1931)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.82 g/LALOGPS
logP1.48ALOGPS
logP1.04ChemAxon
logS-1.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.07 m³·mol⁻¹ChemAxon
Polarizability8.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-61ccd28a5af292bf5a6a2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-61ccd28a5af292bf5a6a2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-61ccd28a5af292bf5a6a2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-44ce54536ff5fca6c3492016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-44ce54536ff5fca6c3492016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0900000000-44ce54536ff5fca6c3492016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dm-9700000000-ae8ef1d984d4e339f3a92014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityBromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (5, 6, 1)
MetabolismBromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (5)
Toxicity ValuesLD50: 3738 mg/kg (Subcutaneous, Mouse) (2) LC50: 40 g/m3 over 2 hours (Inhalation, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt may be produced synthetically or naturally by marine algae. Dibromomethane is used as a solvent, gage fluid and in organic synthesis. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.
Minimum Risk LevelNot Available
Health EffectsBromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (4, 5, 6)
SymptomsBromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (5, 6)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID3024
ChEMBL IDNot Available
ChemSpider ID2916
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID47077
BioCyc IDCPD-10560
CTD IDC027947
Stitch IDDibromomethane
PDB IDNot Available
ACToR ID1569
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1795.pdf
General References
  1. Ziouzenkova O, Orasanu G, Sharlach M, Akiyama TE, Berger JP, Viereck J, Hamilton JA, Tang G, Dolnikowski GG, Vogel S, Duester G, Plutzky J: Retinaldehyde represses adipogenesis and diet-induced obesity. Nat Med. 2007 Jun;13(6):695-702. Epub 2007 May 27. [17529981 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  4. Wikipedia. Bromine. Last Updated 9 June 2009. [Link]
  5. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  6. Wikipedia. Potassium bromide. Last Updated 9 June 2009. [Link]
  7. Wikipedia. 1,2-Dibromoethane. Last Updated 24 May 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available