Record Information
Version1.0
Creation Date2009-06-22 16:08:24 UTC
Update Date2026-03-31 20:17:17 UTC
Accession NumberCHEM001419
Identification
Common NameIsophorone diisocyanate
ClassSmall Molecule
DescriptionIsophorone diisocyanate, also known as IPDI, is a chemical compound of cyanide and an aliphatic diisocyanate. Aliphatic diisocyanates are used in special applications, such as enamel coatings which are resistant to abrasion and degradation from ultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied to aircraft. (3)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cyanide Compound
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
3-Isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanateChEBI
IPDIChEBI
Isocyanic acid, methylene(3,5,5-trimethyl-3,1-cyclohexylene) esterChEBI
Isophorone diamine diisocyanateChEBI
3-Isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanic acidGenerator
Isocyanate, methylene(3,5,5-trimethyl-3,1-cyclohexylene) esterGenerator
Isophorone diamine diisocyanic acidGenerator
Isophorone diisocyanic acidGenerator
Chemical FormulaC12H18N2O2
Average Molecular Mass222.284 g/mol
Monoisotopic Mass222.137 g/mol
CAS Registry Number4098-71-9
IUPAC Name5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane
Traditional Nameisophorone diisocyanate
SMILESCC1(C)CC(CC(C)(CN=C=O)C1)N=C=O
InChI IdentifierInChI=1S/C12H18N2O2/c1-11(2)4-10(14-9-16)5-12(3,6-11)7-13-8-15/h10H,4-7H2,1-3H3
InChI KeyNIMLQBUJDJZYEJ-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 homomonocyclic compound
Molecular FrameworkAliphatic 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
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point158-159°C at 1.50E+01 mm Hg
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP2.41ALOGPS
logP2.13ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.25 m³·mol⁻¹ChemAxon
Polarizability23.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5910000000-c19afc76593fa47648d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0980000000-42c7c2fdf96137f312f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0910000000-4bbecbf9713e6585a049Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01x0-5900000000-4b64defed855560bd0a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2190000000-0de30ae86d208722f0e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9250000000-6156d7e07d2bd9b7d94eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1bb6b7de2c6d6e055362Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0900000000-432861dca6d6eb8c2889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-074i-2900000000-aa9fcdf85289714eaa27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-9320709b371f2ef9bbbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-2960000000-5b2662cf43d5eeb7882dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9600000000-fa1943750a1b1b783a5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-51d283be4237ed8ab376Spectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
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. (2)
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. (1)
Toxicity ValuesLD50: 1060 mg/kg (Dermal, Rabbit) (4) LD50: >1000 mg/kg (Oral, Rat) (5) LC50: 123 mg/m3 over 4 hours (Inhalation, Rat) (5)
Lethal Dose200 to 300 milligrams for an adult human (cyanide salts). (6)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAliphatic diisocyanates are used in special applications, such as enamel coatings which are resistant to abrasion and degradation from ultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied to aircraft. (3)
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. (1, 2)
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. (1, 2)
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. (2)
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 LinkIsophorone_diisocyanate
Chemspider IDNot Available
ChEBI ID53214
PubChem Compound ID169132
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=1447476
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19851844
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20817708
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22237013
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23218325
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23394610
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23484438
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23548862
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23564646
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23648023