1,2-Dibromo-3-chloropropane (CHEM000040)

Record Information
Version1.0
Creation Date2009-03-06 18:57:58 UTC
Update Date2026-08-22 12:57:55 UTC
Accession NumberCHEM000040
Identification
Common Name1,2-Dibromo-3-chloropropane
ClassSmall Molecule
Description
1,2-Dibromo-3-chloropropane is a manufactured chemical and the active ingredient in the nematicide Nemagon, also known as Fumazone. Nemagon is a soil fumigant formerly used in agriculture but banned to most areas today. (3)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Bromide Compound
  • Organic Compound
  • Organobromide
  • Organochloride
  • PMT
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
DBCPKegg
FumazoneMeSH
NemagonMeSH
DibromochloropropaneMeSH
Chemical FormulaC3H5Br2Cl
Average Molecular Mass236.333 g/mol
Monoisotopic Mass233.845 g/mol
CAS Registry Number96-12-8
IUPAC Name1,2-dibromo-3-chloropropane
Traditional Name1,2-dibromo-3-chloropropane
SMILESClCC(Br)CBr
InChI IdentifierInChI=1S/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2
InChI KeyWBEJYOJJBDISQU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganochlorides
Sub ClassNot Available
Direct ParentOrganochlorides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organochloride
  • Organobromide
  • Alkyl halide
  • Alkyl chloride
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytosol
  • Membrane
  • Microsome
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point6°C
Boiling PointNot Available
Solubility1.23 mg/mL at 20 °C [MUNNECKE,DE & VANGUNDY,SD (1979)]
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.95ALOGPS
logP2.6ChemAxon
logS-3.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.64 m³·mol⁻¹ChemAxon
Polarizability14.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
Mechanism of ToxicityThe initial metabolism of 1,2-dibromo-3-chloropropane to reactive epoxide metabolites that bind to DNA and other macromolecules may be responsible for its hepatotoxicity and nephrotoxicity. The mechanism of 1,2-dibromo-3-chloropropane's testicular toxicity is believed to be due to either the inhibition of sperm carbohydrate metabolism, probably at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain, or drect DNA damage caused by its metabolites. (2, 1)
Metabolism1,2-Dibromo-3-chloropropane is absorbed via oral, inhalation, and dermal routes. It accumulates mainly in the kidney, liver, and adipose tissues. 1,2-Dibromo-3-chloropropane is intially converted to epoxy derivatives, which are further hydrolyzed and debrominated. Glutathione (GSH) conjugation of epoxide intermediates in the liver is believed to produce precursors to toxic intermediates. The metabolites are excreted mainly in the urine. (2)
Toxicity ValuesLD50: 100 mg/kg (Oral, Rabbit) (6) LC50: 1480 mg/m3 over 1 hour (Inhalation, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/Sources1,2-Dibromo-3-chloropropane is the active ingredient in the nematicide Nemagon, also known as Fumazone. Nemagon is a soil fumigant formerly used in agriculture. (2)
Minimum Risk LevelIntermediate Inhalation: 0.0002 ppm (4) Intermediate Oral: 0.002 mg/kg/day (4)
Health EffectsBreathing high levels of 1,2-dibromo-3-chloropropane causes reproductive damage, including reduced sperm counts, birth defects, and infertility. It may also damage the stomach, liver, kidneys, brain, spleen, blood, and lungs, and cause skin and eye damage from direct contact. (2)
SymptomsSymptoms of 1,2-dibromo-3-chloropropane exposure include headaches, nausea, lightheadedness, and weakness. (2)
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
External Links
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 Link1,2-Dibromo-3-chloropropane
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID7280
Kegg Compound IDC14336
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References