Record Information
Version1.0
Creation Date2009-06-22 16:08:25 UTC
Update Date2026-04-06 14:10:25 UTC
Accession NumberCHEM001422
Identification
Common NameToluene diisocyanate
ClassSmall Molecule
DescriptionToluene diisocyanate, also know as TDI, is a chemical compound of cyanide and an aromatic diisocyanate with the formula CH3C6H3(NCO)2. It is used in the manufacture of polyurethane. (3) Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is often marketed as 80/20 and 65/35 mixtures of the 2,4 and 2,6 isomers respectively. It is produced on a large scale, accounting for 34.1% of the global isocyanate market in 2000, second only to MDI.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Cyanide Compound
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Pollutant
  • Synthetic Compound
  • Volatile Isocyanate
Chemical Structure
Thumb
Synonyms
ValueSource
Toluene diisocyanic acidGenerator
Chemical FormulaC18H12N4O4
Average Molecular Mass348.312 g/mol
Monoisotopic Mass348.086 g/mol
CAS Registry Number86-91-9
IUPAC Name1,3-diisocyanato-2-methylbenzene; 2,4-diisocyanato-1-methylbenzene
Traditional Name2,6-toluene diisocyanate; toluene diisocyanate
SMILESCC1=C(C=C(C=C1)N=C=O)N=C=O.CC1=C(C=CC=C1N=C=O)N=C=O
InChI IdentifierInChI=1S/2C9H6N2O2/c1-7-2-3-8(10-5-12)4-9(7)11-6-13;1-7-8(10-5-12)3-2-4-9(7)11-6-13/h2*2-4H,1H3
InChI KeyLNKSOGFDOODVSP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as toluene diisocyanates. These are organic compounds containing a benzene ring, which is substituted by a methyl group and two isocyanate groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentToluene diisocyanates
Alternative Parents
Substituents
  • Toluene diisocyanate
  • Isocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cell surface
  • Extracellular
  • Extracellular matrix
  • Membrane
  • Microsome
  • Microtubule
  • Nerve Fiber
  • Plasma Membrane
  • Tubulin
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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.49ALOGPS
logP2.31ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.24 m³·mol⁻¹ChemAxon
Polarizability16.58 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-cb5e9ddc89afbaa378f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-cb5e9ddc89afbaa378f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0009000000-cb5e9ddc89afbaa378f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-bc2245360cd6ee424639Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-bc2245360cd6ee424639Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-bc2245360cd6ee424639Spectrum
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: 1950 mg/kg (Oral, Mouse) (4)
Lethal Dose200 to 300 milligrams for an adult human (cyanide salts). (5)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesToluene diisocyanate is used in the manufacture of polyurethane. (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 LinkToluene diisocyanate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID33518
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available