Record Information
Version1.0
Creation Date2009-06-22 16:08:27 UTC
Update Date2026-03-26 23:52:53 UTC
Accession NumberCHEM001450
Identification
Common NameBromoxynil
ClassSmall Molecule
DescriptionBromoxynil is a chemical compound of cyanide that is used as a herbicide. It is not permitted for homeowner use and is used for mainly for post-emergent control of annual broadleaf weeds. It is especially effective in the control of weeds in cereal, corn, sorghum, onions, flax, mint, turf, and on non-cropland. It works by inhibiting photosynthesis. (4)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Cyanide Compound
  • Herbicide
  • Nitrile
  • Organic Compound
  • Organobromide
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2,6-Dibromo-4-cyanophenolChEBI
3,5-Dibromo-4-hydroxybenzonitrileKegg
Bromoxynil, potassium saltMeSH
Bromoxynil, sodium saltMeSH
Chemical FormulaC7H3Br2NO
Average Molecular Mass276.913 g/mol
Monoisotopic Mass274.858 g/mol
CAS Registry Number1689-84-5
IUPAC Name3,5-dibromo-4-hydroxybenzonitrile
Traditional Namesabre
SMILESOC1=C(Br)C=C(C=C1Br)C#N
InChI IdentifierInChI=1S/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
InChI KeyUPMXNNIRAGDFEH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzonitriles
Direct ParentBenzonitriles
Alternative Parents
Substituents
  • Benzonitrile
  • 2-halophenol
  • 2-bromophenol
  • Bromobenzene
  • Halobenzene
  • Phenol
  • Aryl bromide
  • Aryl halide
  • Nitrile
  • Carbonitrile
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite crystals.
Experimental Properties
PropertyValue
Melting Point190°C
Boiling PointNot Available
Solubility0.13 mg/mL at 25°C [WORTHING,CR & WALKER,SB (1987)]
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP3.19ALOGPS
logP3.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)5.11ChemAxon
pKa (Strongest Basic)-8.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.01 m³·mol⁻¹ChemAxon
Polarizability18.48 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, Positivesplash10-004i-0090000000-a3feeae06376e3d872f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-c5e4e45a063b9e24c3eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0190000000-d7ed228dc94814bf53d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-23e6eedc75d72331cbe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-23e6eedc75d72331cbe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0190000000-da7fd467433222734406Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9370000000-f5a86b589d9ad7960867Spectrum
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6) ; dermal (6)
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (3)
MetabolismOrganic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (2)
Toxicity ValuesLD50: 190 mg/kg (Oral, Rat) (10) LD50: 2000 mg/kg (Dermal, Rat) (8)
Lethal Dose210 to 300 milligrams for an adult human (cyanide salts). (9)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBromoxynil is used as a herbicide. It is not permitted for homeowner use and is used for mainly for post-emergent control of annual broadleaf weeds. It is especially effective in the control of weeds in cereal, corn, sorghum, onions, flax, mint, turf, and on non-cropland. (4)
Minimum Risk LevelNot Available
Health EffectsExposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. Bromine 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. (5, 6, 7, 2, 3)
SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. Bromine 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. (6, 7, 2, 3)
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 LinkBromoxynil
Chemspider IDNot Available
ChEBI ID17192
PubChem Compound ID15531
Kegg Compound IDC04178
YMDB IDNot Available
ECMDB IDM2MDB004768
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11910467
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24458090