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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:04:03 UTC
Update Date2022-09-22 18:34:44 UTC
HMDB IDHMDB0341267
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-(4-Aminophenoxy)aniline
Description4,4'-Oxydianiline, also known as 4-aminophenyl ether, belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. 4,4’-Oxydianiline is an organic compound with the formula O(C6H4NH2)2. Other applications of 4,4’-oxydianiline include the production of poly(amide)imide resins (which are used in the manufacture of heat-resistant wire enamels and coatings), as an intermediate in the manufacture of epoxy resins and adhesives, and in the production of aromatic polyether imides. 4,4'-Oxydianiline is a strong basic compound (based on its pKa). These resins are used for their temperature-resistant properties and are utilized in products including wire enamels, coatings, film, adhesives, insulating varnishes, coated fabrics, flame-retardant fibers, oil sealants and retainers, insulation for cables and printed circuits, and laminates and composite for aerospace vehicles. This colourless solid is a useful monomer and cross-linking agent for polymers, especially the polyimides, such as Kapton.4,4’-Oxydianiline is used in the production of a wide variety of polymer resins. A specific reaction involving industrial use of 4,4’-oxydianiline is in the production of thermostable poly(amideurea) acids, which can be prepared from 4,4’-oxydianiline, pyromellitic dianhydride, and diisocyanates. The primary use lies in the production of polyimide and poly(ester)imide resins. It is an ether derivative of aniline.
Structure
Thumb
Synonyms
ValueSource
4-Aminophenyl etherKegg
4,4'-OxybisbenzenamineKegg
Di-(4-aminophenyl)etherMeSH
Diaminodiphenyl etherMeSH
4,4'-Diaminodiphenyl etherMeSH
4,4'-OxydianilineKEGG
Chemical FormulaC12H12N2O
Average Molecular Weight200.241
Monoisotopic Molecular Weight200.094963014
IUPAC Name4-(4-aminophenoxy)aniline
Traditional Name4,4-oxydianiline
CAS Registry NumberNot Available
SMILES
NC1=CC=C(OC2=CC=C(N)C=C2)C=C1
InChI Identifier
InChI=1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2
InChI KeyHLBLWEWZXPIGSM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Diaryl ether
  • Phenoxy compound
  • Aniline or substituted anilines
  • Phenol ether
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 10V, Positive-QTOFsplash10-0udi-0090000000-85c2073853351036f42e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 20V, Positive-QTOFsplash10-0udi-0090000000-740365794536d488af7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 40V, Positive-QTOFsplash10-0gi3-9400000000-9295f84182a0bc3a24cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 10V, Negative-QTOFsplash10-0002-0900000000-f9c3ffe518c66e89da632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 20V, Negative-QTOFsplash10-0002-0900000000-32b17547146c5d07bf7b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 40V, Negative-QTOFsplash10-0a4m-9600000000-7a9b7692821fe63591a72016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14759
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4,4'-Oxydianiline
METLIN IDNot Available
PubChem Compound7579
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]