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Record Information
Version1.0
Creation Date2009-06-22 16:08:25 UTC
Update Date2016-11-09 01:08:32 UTC
Accession NumberCHEM001423
Identification
Common Namen-Butyl isocyanate
ClassSmall Molecule
Descriptionn-Butyl isocyanate is a chemical compound of cyanide.
Contaminant Sources
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cyanide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
1-Butyl isocyanateChEBI
BICChEBI
Butyl isocyanateChEBI
1-Butyl isocyanic acidGenerator
Butyl isocyanic acidGenerator
N-Butyl isocyanic acidGenerator
N-ButylisocyanateMeSH
Chemical FormulaC5H9NO
Average Molecular Mass99.131 g/mol
Monoisotopic Mass99.068 g/mol
CAS Registry Number111-36-4
IUPAC Name1-isocyanatobutane
Traditional Namebutyl isocyanate
SMILESCCCCN=C=O
InChI IdentifierInChI=1S/C5H9NO/c1-2-3-4-6-5-7/h2-4H2,1H3
InChI KeyHNHVTXYLRVGMHD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassIsocyanates
Direct ParentIsocyanates
Alternative Parents
Substituents
  • Isocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-75°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.21 g/LALOGPS
logP1.46ALOGPS
logP1.28ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.21 m³·mol⁻¹ChemAxon
Polarizability11.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6900000000-2ef5f8a6351d45e73be2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-9200000000-ee7fab04f64e72972396View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-270b3f5a57437164955bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-accc51a0c326dd204271View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-9000000000-a96874878021f3d6177fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5d7d380bdcda275fd3a1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-4a4b6f3428a41defaf2aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityCyanide 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. (5)
MetabolismCyanide is rapidly alsorbed through oral, inhalation, and dermal routes 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. (4)
Toxicity ValuesLD50: 360 mg/kg (Oral, Rat) (2) LD50: 1 mg/kg (Intravenous, Mouse) (1) LC50: 0.5 mg/L over 1 hours (Inhalation, Rat) (2)
Lethal Dose200 to 300 milligrams for an adult human (cyanide salts). (3)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
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. (4, 5)
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. (4, 5)
TreatmentAntidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (5)
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 ID136519
PubChem Compound ID8110
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16091349
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25532938
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6821040