Page last updated: 2024-12-05

di-(4-aminophenyl)ether

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Description

Di-(4-aminophenyl)ether, also known as 4,4'-oxydianiline (ODA), is a colorless crystalline solid. It is a key monomer in the production of high-performance polymers such as poly(ether ether ketone) (PEEK) and poly(ether imide) (PEI), which are used in various applications, including aerospace, automotive, and electronics. The compound is typically synthesized by reacting 4-chloronitrobenzene with potassium hydroxide in the presence of a copper catalyst. ODA is also known for its potential use in organic electronics and as a precursor for the synthesis of other functional materials. Its unique properties, such as its high thermal stability and excellent mechanical strength, make it a subject of ongoing research.'

di-(4-aminophenyl)ether: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID7579
CHEMBL ID354663
CHEBI ID34384
SCHEMBL ID41849
MeSH IDM0064172

Synonyms (117)

Synonym
BIDD:ER0256
CBMICRO_028442
bis(4-aminophenyl) ether
4,4'-oxybisbenzenamine
4,4-oxydianiline
4,4'-diaminodiphenyl ether
ether,4'-diaminodiphenyl-
bis(p-aminophenyl) ether
p,p'-oxybis(aniline)
4,4'-diaminobiphenyl oxide
4,4'-oxydiphenylamine
oxybis(4-aminobenzene)
oxydi-p-phenylenediamine
p,p'-oxydianiline
nsc-6089
4,4-dadpe
101-80-4
4,4'-oxydianiline
wln: zr dor dz
aniline,4'-oxydi-
diaminodiphenyl ether
4,4'-oxybis(aniline)
benzenamine,4'-oxybis-
oxydianiline
p,p'-diaminodiphenyl ether
4,4'-diaminodiphenyl oxide
4,4'-diaminophenyl ether
nsc6089
dadpe
4,4-diaminodiphenyl ether
4-aminophenyl ether
p-aminophenyl ether
nci-c50146
nsc-37075
nsc37075
aniline, 4,4'-oxydi-
benzenamine, 4,4'-oxybis-
4-(4-aminophenoxy)aniline
OPREA1_332864
NCGC00091391-01
BIM-0028242.P001
bis(p-aminophenyl)ether
4,4'-diaminobiphenyloxide
di-(4-aminophenyl)ether
4,4'-diaminophenyl oxide
nsc 37075
4,4'-diaminodiphenyloxide
bis(4-aminophenyl)ether
einecs 202-977-0
4,4'-oxybisaniline
brn 0475735
ccris 491
ether, 4,4'-diaminodiphenyl
hsdb 1316
ai3-18375
4,4'-oxydianiline, 97%
OPREA1_805797
4,4'-oxydianiline, purified by sublimation, 99%
NCGC00091391-02
STK046240
AC-11212
AKOS000118817
chebi:34384 ,
CHEMBL354663
O0088
NCGC00091391-04
NCGC00091391-03
NCGC00253956-01
dtxsid0021094 ,
tox21_202035
cas-101-80-4
tox21_300133
NCGC00259584-01
dtxcid401094
BBL012119
CCG-105139
28dlb4z70t ,
ec 202-977-0
unii-28dlb4z70t
FT-0617023
PS-5282
4-(4-aminophenoxy)phenylamine
4,4'-diaminodiphenyl ether [iarc]
dpe (amine)
p-diaminodiphenylether
1-amino-4-(4-aminophenoxy)benzene
4,4'-oxybis(benzenamine)
bis(4-aminophenyl) ether [hsdb]
4,4'-oda
SCHEMBL41849
cambridge id 5493582
4,4'diaminodiphenylether
W-108902
di(4-aminophenyl) ether
4,4'-oxybis[aniline]
ether, 4,4'-diaminodiphenyl-
4-(4-aminophenoxy)phenylamine #
oxybis[4-aminobenzene]
mfcd00007863
4,4'-oxydianiline, zone-refined, purified by sublimation, >=99%
4,4'-oxydianiline, analytical standard
EN300-16780
sr-01000414668
SR-01000414668-1
4-aminophenylether
4-aminophenylether (4,4'-oxydianiline)
121509-79-3
Z56775415
Q3704503
E76010
4,4'-diamino diphenylether
AMY40782
4,4'-oxydianiline (oda)
4,4'-biaminodiphenyl ether
YSWG195
A930210
CS-W015612
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (34)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency44.66840.004023.8416100.0000AID485290
LuciferasePhotinus pyralis (common eastern firefly)Potency63.26090.007215.758889.3584AID1224835
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
thyroid stimulating hormone receptorHomo sapiens (human)Potency1.25890.001318.074339.8107AID926; AID938
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency49.57670.000657.913322,387.1992AID1259377; AID1259378
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency43.03510.001022.650876.6163AID1224838; AID1224839; AID1224893
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency50.11870.000214.376460.0339AID588533
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency56.24290.003041.611522,387.1992AID1159552; AID1159553; AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency54.94100.000817.505159.3239AID1159527; AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency62.33800.001530.607315,848.9004AID1224848; AID1224849; AID1259403
farnesoid X nuclear receptorHomo sapiens (human)Potency0.00100.375827.485161.6524AID588527
pregnane X nuclear receptorHomo sapiens (human)Potency65.29570.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency37.85740.000229.305416,493.5996AID588514; AID743075
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency39.81070.001024.504861.6448AID588534
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency44.66840.001019.414170.9645AID588537
aryl hydrocarbon receptorHomo sapiens (human)Potency21.84250.000723.06741,258.9301AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency62.02500.001723.839378.1014AID743083
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency31.62280.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID446999Anticonvulsant activity in Sprague-Dawley rat assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, po after 2 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID115843Compound was tested for the number of control mice with decreased RBC to that of number of tested mice at 100 mg/kg p.o.; 4/51998Bioorganic & medicinal chemistry letters, Jan-06, Volume: 8, Issue:1
Discovery of FR115092: a novel antinephritic agent.
AID433903Hepatotoxicity in mouse assessed as carcinogenic potency2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Development of QSAR models for predicting hepatocarcinogenic toxicity of chemicals.
AID446991Anticonvulsant activity in CF1 albino mouse assessed as inhibition of maximal electric shock-induced seizure at 100 mg/kg, ip after 0.5 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446990Anticonvulsant activity in CF1 albino mouse assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, ip after 0.5 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446993Anticonvulsant activity in CF1 albino mouse assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, ip after 4 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID117036Inhibition of proteinuria in the graft-versus-host disease mice following 100 mg/kg p.o. administration.1998Bioorganic & medicinal chemistry letters, Jan-06, Volume: 8, Issue:1
Discovery of FR115092: a novel antinephritic agent.
AID446994Anticonvulsant activity in CF1 albino mouse assessed as inhibition of maximal electric shock-induced seizure at 100 mg/kg, ip after 4 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID1072104Cytotoxicity against human Hep3B cells after 6 hrs by MTT assay2014European journal of medicinal chemistry, Mar-03, Volume: 744,4'-Diaminodiphenyl ether derivatives: synthesis, spectral, optical, thermal characterization and in-vitro cytotoxicity against Hep 3B and IMR 32 human cell lines.
AID447142Neurotoxicity in Sprague-Dawley rat at 30 mg/kg, po by positional sense and gait and stance test2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446996Anticonvulsant activity in Sprague-Dawley rat assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, po after 0.25 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID1072105Cytotoxicity against human IMR32 cells after 6 hrs by MTT assay2014European journal of medicinal chemistry, Mar-03, Volume: 744,4'-Diaminodiphenyl ether derivatives: synthesis, spectral, optical, thermal characterization and in-vitro cytotoxicity against Hep 3B and IMR 32 human cell lines.
AID447000Anticonvulsant activity in Sprague-Dawley rat assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, po after 4 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446997Anticonvulsant activity in Sprague-Dawley rat assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, po after 0.5 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446998Anticonvulsant activity in Sprague-Dawley rat assessed as inhibition of maximal electric shock-induced seizure at 30 mg/kg, po after 1 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446992Anticonvulsant activity in CF1 albino mouse assessed as inhibition of maximal electric shock-induced seizure at 300 mg/kg, ip after 0.5 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID446995Anticonvulsant activity in CF1 albino mouse assessed as inhibition of maximal electric shock-induced seizure at 300 mg/kg, ip after 4 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
In vivo evaluation of diaminodiphenyls: anticonvulsant agents with minimal acute neurotoxicity.
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (26.09)18.7374
1990's4 (17.39)18.2507
2000's5 (21.74)29.6817
2010's7 (30.43)24.3611
2020's1 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.37 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]