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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:04:03 UTC

Update Date

2022-09-22 18:34:44 UTC

HMDB ID

HMDB0341267

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(4-Aminophenoxy)aniline

Description

4,4'-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

MOL SDF PDB SMILES InChI


  Mrv1572004191601112D          

 15 16  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341267

> <DATABASE_NAME>
hmdb

> <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_KEY>
HLBLWEWZXPIGSM-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O

> <MOLECULAR_WEIGHT>
200.241

> <EXACT_MASS>
200.094963014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.407768565164176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-aminophenoxy)aniline

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.8156810909999996

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.638934066212018

> <JCHEM_POLAR_SURFACE_AREA>
61.269999999999996

> <JCHEM_REFRACTIVITY>
61.69960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4-oxydianiline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      12.003   6.930   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    5    9                                                       
CONECT    2    6    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    4   14                                                  
CONECT   11    5    6   15                                                  
CONECT   12    7    8   15                                                  
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Aminophenyl ether	Kegg
4,4'-Oxybisbenzenamine	Kegg
Di-(4-aminophenyl)ether	MeSH
Diaminodiphenyl ether	MeSH
4,4'-Diaminodiphenyl ether	MeSH
4,4'-Oxydianiline	KEGG

Chemical Formula

C₁₂H₁₂N₂O

Average Molecular Weight

200.241

Monoisotopic Molecular Weight

200.094963014

IUPAC Name

4-(4-aminophenoxy)aniline

Traditional Name

4,4-oxydianiline

CAS Registry Number

Not 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 Key

HLBLWEWZXPIGSM-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:34384 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.87	ALOGPS
logP	1.82	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	4.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.27 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.7 m³·mol⁻¹	ChemAxon
Polarizability	21.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 10V, Positive-QTOF	splash10-0udi-0090000000-85c2073853351036f42e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 20V, Positive-QTOF	splash10-0udi-0090000000-740365794536d488af7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 40V, Positive-QTOF	splash10-0gi3-9400000000-9295f84182a0bc3a24cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 10V, Negative-QTOF	splash10-0002-0900000000-f9c3ffe518c66e89da63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 20V, Negative-QTOF	splash10-0002-0900000000-32b17547146c5d07bf7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Aminophenoxy)aniline 40V, Negative-QTOF	splash10-0a4m-9600000000-7a9b7692821fe63591a7	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14759

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,4'-Oxydianiline

METLIN ID

Not Available

PubChem Compound

7579

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for 4-(4-Aminophenoxy)aniline (HMDB0341267)

MOL for HMDB0341267 (4-(4-Aminophenoxy)aniline)

3D MOL for HMDB0341267 (4-(4-Aminophenoxy)aniline)

3D SDF for HMDB0341267 (4-(4-Aminophenoxy)aniline)

3D-SDF for HMDB0341267 (4-(4-Aminophenoxy)aniline)

PDB for HMDB0341267 (4-(4-Aminophenoxy)aniline)

3D PDB for HMDB0341267 (4-(4-Aminophenoxy)aniline)

SMILES for HMDB0341267 (4-(4-Aminophenoxy)aniline)

INCHI for HMDB0341267 (4-(4-Aminophenoxy)aniline)

Structure for HMDB0341267 (4-(4-Aminophenoxy)aniline)

3D Structure for HMDB0341267 (4-(4-Aminophenoxy)aniline)

Predicted Retention Times

Predicted Kovats Retention Indices

MS/MS Spectra