Methylene bis(4-cyclohexylisocyanate) (CHEM001429)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (39)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:25 UTC
Update Date2026-03-26 21:48:37 UTC
Accession NumberCHEM001429
Identification
Common NameMethylene bis(4-cyclohexylisocyanate)
ClassSmall Molecule
DescriptionMethylene bis(4-cyclohexylisocyanate) is a chemical compound of cyanide.
Contaminant Sources
  • Clean Air Act Chemicals
  • 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,4'-DiisocyanatodicyclohexylmethaneChEBI
4,4'-Methylenedi(cyclohexyl isocyanate)ChEBI
Bis(4-isocyanatocyclohexyl)methaneChEBI
Dicyclohexylmethane 4,4'-diisocyanateChEBI
Dicyclohexylmethane-4,4'-di-isocyanateChEBI
HMDIChEBI
Hydrogenated mdiChEBI
Hylene WChEBI
Isocyanic acid, methylenedi-4,1-cyclohexylene esterChEBI
Methylene bis-(4-cyclohexylisocyanate)ChEBI
4,4'-Methylenedi(cyclohexyl isocyanic acid)Generator
Dicyclohexylmethane 4,4'-diisocyanic acidGenerator
Dicyclohexylmethane-4,4'-di-isocyanic acidGenerator
Isocyanate, methylenedi-4,1-cyclohexylene esterGenerator
Methylene bis-(4-cyclohexylisocyanic acid)Generator
Methylene bis(4-cyclohexylisocyanic acid)Generator
Methylene bis(4-cyclohexylisocyanate), (trans-trans)-isomerMeSH
Dicyclohexylmethane-4,4'-diisocyanateMeSH
HMDI CPDMeSH
4,4-Methylene biscyclohexyl diisocyanateMeSH
Chemical FormulaC15H22N2O2
Average Molecular Mass262.347 g/mol
Monoisotopic Mass262.168 g/mol
CAS Registry Number5124-30-1
IUPAC Name1-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexane
Traditional NameHMDI
SMILESO=C=NC1CCC(CC2CCC(CC2)N=C=O)CC1
InChI IdentifierInChI=1S/C15H22N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h12-15H,1-9H2
InChI KeyKORSJDCBLAPZEQ-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 Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.98ALOGPS
logP3.18ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.4 m³·mol⁻¹ChemAxon
Polarizability29.91 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-00fr-2920000000-0c94def34397a34f48d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-534aa45a1d066610b6ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-2960000000-71c522e2d1c1daec9499Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9820000000-adca25992b6ad9ad91d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-45f460f14583b9f39337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3090000000-ce3cf414e55d5e272e72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5967e7479c7390704b67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02g9-0190000000-1791c7a112d2dfae44dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1390000000-28c5b8c1166209bd5396Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00c3-4930000000-ac3d778288cb80824323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0090000000-3da56d4bf3a0a0bdcd0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-3039fb3457d68fe3b19fSpectrum
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 ValuesLC50: 0.307 mg/L over 4 hours (Inhalation, Rat) (3)
Lethal Dose200 to 300 milligrams for an adult human (cyanide salts). (4)
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. (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 LinkNot Available
Chemspider IDNot Available
ChEBI ID53216
PubChem Compound ID21202
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=11603590
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1447476
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14531868
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17896759
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19804698
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20004749
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20334402
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20851382
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=2488962
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6740674
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6821040
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8960156