Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-10 21:27:21 UTC |
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Update Date | 2021-09-26 22:51:56 UTC |
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HMDB ID | HMDB0244288 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 4,4'-Methylenebis(2-chloroaniline) |
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Description | 4,4'-Methylenebis(2-chloroaniline), also known as MOCA, 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. 4,4'-Methylenebis(2-chloroaniline) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4,4'-Methylenebis(2-chloroaniline) is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a small amount of articles have been published on 4,4'-Methylenebis(2-chloroaniline). This compound has been identified in human blood as reported by (PMID: 31557052 ). 4,4'-methylenebis(2-chloroaniline) is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4,4'-Methylenebis(2-chloroaniline) is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2 |
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Synonyms | Value | Source |
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Methylenebis(chloroaniline) | ChEBI | MOCA | ChEBI | 3,3'-Dichloro-4,4'-diaminodiphenylmethane | HMDB | Methylene bis(chloroaniline) | HMDB | MBOCA | HMDB |
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Chemical Formula | C13H12Cl2N2 |
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Average Molecular Weight | 267.154 |
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Monoisotopic Molecular Weight | 266.037753808 |
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IUPAC Name | 4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline |
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Traditional Name | bis amine |
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CAS Registry Number | Not Available |
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SMILES | NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl |
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InChI Identifier | InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2 |
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InChI Key | IBOFVQJTBBUKMU-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
- Halobenzene
- Chlorobenzene
- Aryl halide
- Aryl chloride
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4,4'-Methylenebis(2-chloroaniline),1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl | 2555.8 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl | 2428.0 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl | 3278.2 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C(Cl)=C2)C=C1Cl | 2633.1 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C(Cl)=C2)C=C1Cl | 2443.1 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C(Cl)=C2)C=C1Cl | 2841.5 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C | 2466.8 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C | 2525.2 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C | 3061.0 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),3TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl | 2552.5 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),3TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl | 2492.6 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),3TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl | 2699.8 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),4TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C | 2512.3 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),4TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C | 2551.1 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),4TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C | 2539.3 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl | 2756.4 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl | 2666.7 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl | 3325.6 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl | 3038.8 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl | 2927.5 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl | 3031.5 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C | 2903.4 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C | 2930.7 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C | 3137.6 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl | 3187.9 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl | 3107.5 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl | 2986.3 | Standard polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C | 3369.3 | Semi standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C | 3277.9 | Standard non polar | 33892256 | 4,4'-Methylenebis(2-chloroaniline),4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C | 2908.7 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) GC-MS (Non-derivatized) - 70eV, Positive | splash10-014l-0890000000-d320fad1a29793ad1cd3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0159-2690000000-cb107296d1f635b2a12a | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Positive-QTOF | splash10-014i-0090000000-ac6db8aa96928a715ff0 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Positive-QTOF | splash10-014i-0390000000-5200973976fe40d343c8 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Positive-QTOF | splash10-0h93-0790000000-9bffe8b198bbfea28e82 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Negative-QTOF | splash10-014i-0090000000-a39ca28199798c1d03b2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Negative-QTOF | splash10-014i-0090000000-ea98e6716aef094aff27 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Negative-QTOF | splash10-016r-2590000000-6da5025dcc24706340ad | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Positive-QTOF | splash10-014i-0090000000-56429813ec6e144d5baa | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Positive-QTOF | splash10-014i-0090000000-388bf1eeaceec6102241 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Positive-QTOF | splash10-0002-0950000000-0208d8e66ffecbcf4b9e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Negative-QTOF | splash10-014i-3090000000-685f6029d831cae1342b | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Negative-QTOF | splash10-0159-6090000000-189ae8cf88e4d83e80f0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Negative-QTOF | splash10-001i-9110000000-6f3606859a73a43fab2c | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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