Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 02:04:13 UTC |
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Update Date | 2014-12-24 20:26:54 UTC |
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Accession Number | T3D4672 |
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Identification |
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Common Name | 4,4'-Methylenedianiline |
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Class | Small Molecule |
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Description | 4,4'-methylenedianiline belongs to the family of Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups[1]. |
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Compound Type | - Amine
- Industrial/Workplace Toxin
- Metabolite
- Organic Compound
- Pollutant
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 4, 4'-Diphenylmethanediamine | 4, 4'-Methylenebis(aniline) | 4,4'-Diaminodiphenylmethan | 4,4'-Diaminodiphenylmethane | 4,4'-Diphenylmethanediamine | 4,4'-Methylene(bisaniline) | 4,4'-Methylene-Dianiline | 4,4'-Methylenebis(benzeneamine) | 4,4'-Methylenebis-Benzenamine | 4,4'-Methylenebis[aniline] | 4,4'-Methylenedi-Aniline | 4,4'-Methylenedibenzenamine | 4,4-Methylenedianiline | 4-(4-Aminobenzyl)aniline | 4-(4-Aminobenzyl)phenylamine | alpha-(p-Aminophenyl)-p-Toluidine | Ancamine TL | Araldite hardener 972 | Bis(4-aminophenyl)methane | Bis(aminophenyl)methane | Bis(p-aminophenyl)methane | Bis-p-aminofenylmethan | Curithane | DADPM | DAPM | DDM | Di(4-aminophenyl)methane | Di-(4-aminophenyl)methane | Diaminodiphenylmethane | Dianilinemethane | Dianilinomethane | Epicure DDM | Epikure DDM | Jeffamine AP-20 | MDA | Methylenebis(aniline) | Methylenebis[aniline] | Methylenedianiline | p, p'-Methylenedianiline | p,p'-Diaminodifenylmethan | p,p'-Diaminodiphenylmethane | p,p'-Methylenedianiline | Sumicure M | Tonox |
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Chemical Formula | C13H14N2 |
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Average Molecular Mass | 198.264 g/mol |
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Monoisotopic Mass | 198.116 g/mol |
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CAS Registry Number | 101-77-9 |
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IUPAC Name | 4-[(4-aminophenyl)methyl]aniline |
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Traditional Name | 4,4'-diaminodiphenylmethane |
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SMILES | NC1=CC=C(CC2=CC=C(N)C=C2)C=C1 |
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InChI Identifier | InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2 |
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InChI Key | InChIKey=YBRVSVVVWCFQMG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylmethanes |
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Direct Parent | Diphenylmethanes |
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Alternative Parents | |
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Substituents | - Diphenylmethane
- Aniline or substituted anilines
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 92.5 °C | Boiling Point | Not Available | Solubility | 1 mg/mL at 25 °C | LogP | 1.59 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052b-1900000000-a1316bc903c186c14318 | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0900000000-4644a7dbb46f9d7b2ba1 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000t-0900000000-a4548ac0cc34b55b0737 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pe9-3900000000-4cb485ecb653179900c3 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-31a3645696c4f9d211ba | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-0e89f98c9bcf3071812e | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000w-4900000000-9cfc5d89ecd51b783c25 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-d89ea9976ffd35a15c71 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-2900000000-5ccfe3083b2af59df353 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004l-7900000000-07b5c14a9b509e0f3922 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-d2d648aa4423d0c7a455 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-d2d648aa4423d0c7a455 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-1900000000-b08e84c052ca33f2d5b9 | 2021-09-24 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0002-1900000000-3ade5e930b45bb46e746 | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Inhalation, oral, dermal |
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Mechanism of Toxicity | After 4,4'-Methylenedianiline enters to our body, it is transported in the blood or stored in tissues. The N-N-acetylation of the compound leads to the formation of some toxic derivatives. The liver and thyroid are the targets of 4,4'-methylenedianiline in animals. |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. (5) |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB41808 |
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PubChem Compound ID | 7577 |
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ChEMBL ID | CHEMBL85728 |
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ChemSpider ID | 7296 |
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KEGG ID | C14288 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 32506 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D4672.pdf |
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General References | - Pludro G, Karlowski K, Mankowska M, Woggon H, Uhde WJ: [Toxicological and chemical studies of some epoxy resins and hardeners. I. Study of acute and subacute toxicity of phthalic acid anhydride, 4,4'diaminodiphenylmethane and epoxy resin Epilox EG-34]. Acta Pol Pharm. 1969;26(4):353-8. [5349261 ]
- Yasuda SK: Determination of 3,3'-dichloro-4,4'-diaminodiphenylmethane in air. J Chromatogr. 1975 Feb 12;104(2):283-90. [1150762 ]
- Manis MO, Braselton WE Jr: Structure elucidation and in vitro reactivity of the major metabolite of 4,4'-methylenebis(2-chloroaniline) (MBOCA) in canine urine. Fundam Appl Toxicol. 1984 Dec;4(6):1000-8. [6549168 ]
- ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological profile for methylenedianiline. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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