ContaminantDB: Methylene diphenyl diisocyanate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (39)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:25 UTC

Update Date

2026-03-27 01:52:38 UTC

Accession Number

CHEM001421

Identification

Common Name

Methylene diphenyl diisocyanate

Class

Small Molecule

Description

Methylene diphenyl diisocyanate, also know as MDI, is a chemical compound of cyanide and an aromatic diisocyanate. It is used in the manufacture of polyurethane and as an an industrial strength adhesive. (4)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 3
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Cyanide Compound
Household Toxin
Industrial/Workplace Toxin
Organic Compound
Pollutant
Synthetic Compound
Volatile Isocyanate

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1'-Methylenebis(4-isocyanatobenzene)	ChEBI
4,4'-Diisocyanatodiphenylmethane	ChEBI
4,4'-Diphenylmethane diisocyanate	ChEBI
4,4'-Methylene diphenyl diisocyanate	ChEBI
4,4'-Methylenebis(phenyl isocyanate)	ChEBI
4,4'-Methylenedi(phenyl isocyanate)	ChEBI
4,4'-Methylenedi-p-phenylene diisocyanate	ChEBI
4,4'-Methylenediphenyl diisocyanate	ChEBI
4,4'-Methylenediphenyl isocyanate	ChEBI
4,4'-Methylenediphenylene diisocyanate	ChEBI
4,4'-Methylenediphenylene isocyanate	ChEBI
4-4'-Diisocyanate de diphenylmethane	ChEBI
Bis(1,4-isocyanatophenyl)methane	ChEBI
Bis(4-isocyanatophenyl)methane	ChEBI
Bis(p-isocyanatophenyl)methane	ChEBI
Bis(para-isocyanatophenyl)methane	ChEBI
Diphenyl methane diisocyanate	ChEBI
Diphenylmethan-4,4'-diisocyanat	ChEBI
Diphenylmethane diisocyanate	ChEBI
Diphenylmethyl diisocyanate	ChEBI
MDI	ChEBI
MDR	ChEBI
Methylbisphenyl isocyanate	ChEBI
Methylene bisphenyl isocyanate	ChEBI
Methylene di-p-phenylene isocyanate	ChEBI
Methylene diphenyl diisocyanate	ChEBI
Methylenebis(4-isocyanatobenzene)	ChEBI
Methylenebis(4-phenyl isocyanate)	ChEBI
Methylenebis(4-phenylene isocyanate)	ChEBI
Methylenebis(p-phenyl isocyanate)	ChEBI
Methylenebis(p-phenylene isocyanate)	ChEBI
Methylenebis(para-phenyl isocyanate)	ChEBI
Methylenebis(para-phenylene isocyanate)	ChEBI
Methylenebisphenyl diisocyanate	ChEBI
Methylenedi-p-phenylene diisocyanate	ChEBI
Methylenedi-para-phenylene diisocyanate	ChEBI
p,P'-diphenylmethane diisocyanate	ChEBI
p,P'-methylenebis(phenyl isocyanate)	ChEBI
Para,para'-diphenylmethane diisocyanate	ChEBI
Para,para'-methylenebis(phenyl isocyanate)	ChEBI
4,4'-Diphenylmethane diisocyanic acid	Generator
4,4'-Methylene diphenyl diisocyanic acid	Generator
4,4'-Methylenebis(phenyl isocyanic acid)	Generator
4,4'-Methylenedi(phenyl isocyanic acid)	Generator
4,4'-Methylenedi-p-phenylene diisocyanic acid	Generator
4,4'-Methylenediphenyl diisocyanic acid	Generator
4,4'-Methylenediphenyl isocyanic acid	Generator
4,4'-Methylenediphenylene diisocyanic acid	Generator
4,4'-Methylenediphenylene isocyanic acid	Generator
4-4'-Diisocyanic acid de diphenylmethane	Generator
Diphenyl methane diisocyanic acid	Generator
Diphenylmethane diisocyanic acid	Generator
Diphenylmethyl diisocyanic acid	Generator
Methylbisphenyl isocyanic acid	Generator
Methylene bisphenyl isocyanic acid	Generator
Methylene di-p-phenylene isocyanic acid	Generator
Methylene diphenyl diisocyanic acid	Generator
Methylenebis(4-phenyl isocyanic acid)	Generator
Methylenebis(4-phenylene isocyanic acid)	Generator
Methylenebis(p-phenyl isocyanic acid)	Generator
Methylenebis(p-phenylene isocyanic acid)	Generator
Methylenebis(para-phenyl isocyanic acid)	Generator
Methylenebis(para-phenylene isocyanic acid)	Generator
Methylenebisphenyl diisocyanic acid	Generator
Methylenedi-p-phenylene diisocyanic acid	Generator
Methylenedi-para-phenylene diisocyanic acid	Generator
p,P'-diphenylmethane diisocyanic acid	Generator
p,P'-methylenebis(phenyl isocyanic acid)	Generator
Para,para'-diphenylmethane diisocyanic acid	Generator
Para,para'-methylenebis(phenyl isocyanic acid)	Generator
Diphenylmethane-4,4'-diisocyanic acid	Generator
1,1-Methylenebis(phenyl)diisocyanate	MeSH
4,4'-Methylenebis(phenylisocyanate)	MeSH
4,4'-Methylene bisphenyl diisocyanate	MeSH
Diphenylmethane-4,4'-diisocyanate	MeSH
Methylenebis(phenyl isocyanate)	MeSH

Chemical Formula

C₁₅H₁₀N₂O₂

Average Molecular Mass

250.252 g/mol

Monoisotopic Mass

250.074 g/mol

CAS Registry Number

101-68-8

IUPAC Name

1-isocyanato-4-[(4-isocyanatophenyl)methyl]benzene

Traditional Name

diphenylmethane diisocyanate

SMILES

O=C=NC1=CC=C(CC2=CC=C(C=C2)N=C=O)C=C1

InChI Identifier

InChI=1S/C15H10N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h1-8H,9H2

InChI Key

UPMLOUAZCHDJJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

diisocyanate (CHEBI:53218 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	38°C
Boiling Point	314°C (587°K)
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.24	ALOGPS
logP	3.88	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.94 m³·mol⁻¹	ChemAxon
Polarizability	25.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-1890000000-01a5b7c88be700f0a21d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-5c2a926cab6b618bc3a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-5c2a926cab6b618bc3a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-4980000000-bda615052c35c811411c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-b36921e3051707453ad4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-b36921e3051707453ad4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2190000000-c6255f479738de374c50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0190000000-739eadb38c6b8c94f203	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0290000000-4618d9a59227b80d7022	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-0910000000-bef0122d76c4afba60c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-6971a302c8bdd54e5834	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dj-0090000000-d99a8854a86d9097d674	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006y-2950000000-f13713242be7a3d6e97b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-2490000000-3be85aeffd065c857bd3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

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. (2)

Metabolism

Cyanide 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 Values

LD50: 369 mg/m3 over 4 hours (Inhalation, Rat) (5)

Lethal Dose

200 to 300 milligrams for an adult human (cyanide salts). (6)

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (3)

Uses/Sources

Methylene diphenyl diisocyanate is used in the manufacture of polyurethane and as an an industrial strength adhesive. (4)

Minimum Risk Level

Not Available

Health Effects

Exposure 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)

Symptoms

Cyanide 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)

Treatment

Antidotes 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

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0246605

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID