Product Name

  • Name

    4,4'-Oxydianiline

  • EINECS 202-977-0
  • CAS No. 101-80-4
  • Article Data60
  • CAS DataBase
  • Density 1.216 g/cm3
  • Solubility Insoluble in water
  • Melting Point 188-192 °C(lit.)
  • Formula C12H12N2O
  • Boiling Point 389.4 °C at 760 mmHg
  • Molecular Weight 200.24
  • Flash Point 218.9 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance odorless colorless crystals or an odorless fine, beige powder
  • Safety 53-45-61-36/37-26-20
  • Risk Codes 45-46-23/24/25-51/53-62-36/37/38-22
  • Molecular Structure Molecular Structure of 101-80-4 (4,4'-Oxydianiline)
  • Hazard Symbols ToxicT,DangerousN
  • Synonyms 4,4'-Diaminobiphenyl oxide;4,4'-Diaminodiphenyl ether;4,4'-Diaminodiphenyl oxide;4,4'-Diaminophenylether;4,4'-Oxybis(aniline);4,4'-Oxybis[benzenamine];Aniline,4,4'-oxydi- (6CI,8CI);4,4'-Diaminobiphenyl ether;
  • PSA 61.27000
  • LogP 3.80570

Synthetic route

bis(4-nitrophenyl)ether
101-63-3

bis(4-nitrophenyl)ether

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 48h; Autoclave;99%
Stage #1: bis(4-nitrophenyl)ether With pyrographite In N,N-dimethyl-formamide at 140℃; for 2h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In N,N-dimethyl-formamide at 140℃; under 7500.75 Torr; for 5h; Temperature;		99.5%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h;98%
bis(4-iodophenyl) ether
28896-49-3

bis(4-iodophenyl) ether

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With ammonium hydroxide; caesium carbonate98%
4,4'-dinitrosodiphenyl ether

4,4'-dinitrosodiphenyl ether

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With hydrogen In ethanol at 75 - 80℃; under 22502.3 Torr; Autoclave;90.8%
2-Iodo-4-nitro-1-(4-nitro-phenoxy)-benzene
76263-55-3

2-Iodo-4-nitro-1-(4-nitro-phenoxy)-benzene

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With copper(I) chloride; potassium borohydride In methanol for 0.5h; Ambient temperature;82%
4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With aluminum (III) chloride; caesium carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(pinacol)diborane In N,N-dimethyl-formamide at 152℃; for 6h;80%
Multi-step reaction with 2 steps
1.1: sodium hydride / dimethyl sulfoxide / 0.17 h / 20 °C
1.2: 80 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / dimethyl sulfoxide / 12 h / 80 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
View Scheme
nitrobenzene
98-95-3

nitrobenzene

A

4-amino-phenol
123-30-8

4-amino-phenol

B

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

C

aniline
62-53-3

aniline

D

2-amino-phenol
95-55-6

2-amino-phenol

Conditions
ConditionsYield
With hypophosphorous acid; palladium on activated charcoal In water at 80℃; for 4h; Product distribution; var. of temp., ratio, degree of conversion, solvent, catalyst;A 47%
B n/a
C n/a
D n/a
...Expand
diphenylether
101-84-8

diphenylether

A

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

B

4-phenoxyanilin
139-59-3

4-phenoxyanilin

C

2-phenoxyaniline
2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h;A 19.8%
B 19.8%
C 39.5%
...Expand
4,4'-dichlorodiphenyl ether
2444-89-5

4,4'-dichlorodiphenyl ether

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With copper(I) oxide; ammonia; water at 170℃;
4,4'-dibromodiphenyl ether
2050-47-7

4,4'-dibromodiphenyl ether

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With copper(I) oxide; ammonia; water at 170℃;
With ammonium hydroxide; caesium carbonate In ethanol; water at 130℃; for 24h; Inert atmosphere; Sealed tube;
N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With sulfuric acid
sulfuric acid
7664-93-9

sulfuric acid

N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

A

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

B

4-anilinophenol
122-37-2

4-anilinophenol

C

aniline
62-53-3

aniline

D

p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

...Expand
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / K2CO3 / dimethylformamide / 10 h / 145 - 150 °C
2: 95 percent / NH2NH2; FeCl3; activated charcoal / dioxane
View Scheme
Multi-step reaction with 2 steps
1: KOH / dimethylformamide
2: hydrazine hydrate / Raney-nickel
View Scheme
Multi-step reaction with 2 steps
1: 230 °C
2: tin; hydrochloric acid; alcohol
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 145 - 150 °C / Inert atmosphere
2: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / dimethyl sulfoxide / 0.17 h / 20 °C
1.2: 80 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
View Scheme
4-nitrophenol sodium salt
824-78-2

4-nitrophenol sodium salt

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / K2CO3 / dimethylformamide / 10 h / 145 - 150 °C
2: 95 percent / NH2NH2; FeCl3; activated charcoal / dioxane
View Scheme
4-nitro-phenol
100-02-7

4-nitro-phenol

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH / dimethylformamide
2: hydrazine hydrate / Raney-nickel
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 145 - 150 °C / Inert atmosphere
2: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 6 h / Reflux
View Scheme
diphenylether
101-84-8

diphenylether

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: fuming nitric acid
2: tin; hydrochloric acid
View Scheme
potassium 4-nitrophenolate
1124-31-8

potassium 4-nitrophenolate

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 230 °C
2: tin; hydrochloric acid; alcohol
View Scheme
benzenediazonium sulphate

benzenediazonium sulphate

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: fuming nitric acid
3: tin; hydrochloric acid
View Scheme
phenol
108-95-2

phenol

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: fuming nitric acid
3: tin; hydrochloric acid
View Scheme
4-amino-phenol
123-30-8

4-amino-phenol

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / dimethyl sulfoxide / 0.17 h / 20 °C
1.2: 80 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
View Scheme
1,4,7,10,17,20,23,26-octaoxa<10.10>m-cyclophane-13,29-dicarboxylic acid
72606-99-6

1,4,7,10,17,20,23,26-octaoxa<10.10>m-cyclophane-13,29-dicarboxylic acid

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer, Mn 36.0 kg/mol by GPC, Mw/Mn 5.24; monomer(s): bis(5-carboxy-1,3-phenylene)-26-crown-8; 4,4\-oxydianiline

polymer, Mn 36.0 kg/mol by GPC, Mw/Mn 5.24; monomer(s): bis(5-carboxy-1,3-phenylene)-26-crown-8; 4,4\-oxydianiline

Conditions
ConditionsYield
With pyridine; triphenyl phosphite; lithium chloride In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;100%
isophthalic acid
121-91-5

isophthalic acid

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer, Mn 82.2 kg/mol by GPC, Mw/Mn 1.69; monomer(s): isophthalic acid; 4,4\-oxydianiline

polymer, Mn 82.2 kg/mol by GPC, Mw/Mn 1.69; monomer(s): isophthalic acid; 4,4\-oxydianiline

Conditions
ConditionsYield
With pyridine; triphenyl phosphite; lithium chloride In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;100%
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

bis(5-carboxy-1,3-phenylene)-14-crown-4

bis(5-carboxy-1,3-phenylene)-14-crown-4

polymer; monomer(s): bis(5-carboxy-1,3-phenylene)-14-crown-4; 4,4\-oxydianiline

polymer; monomer(s): bis(5-carboxy-1,3-phenylene)-14-crown-4; 4,4\-oxydianiline

Conditions
ConditionsYield
With pyridine; triphenyl phosphite; lithium chloride In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;100%
formaldehyd
50-00-0

formaldehyd

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

2-(nitromethylene)thiazolidine

2-(nitromethylene)thiazolidine

6,6'-(4,4'-oxybis(4,1-phenylene))bis(8-nitro-3,5,6,7-tetrahydro-2H-thiazolo[3,2-c]pyrimidine)
1575814-59-3

6,6'-(4,4'-oxybis(4,1-phenylene))bis(8-nitro-3,5,6,7-tetrahydro-2H-thiazolo[3,2-c]pyrimidine)

Conditions
ConditionsYield
In water at 90℃; for 0.05h; Mannich Aminomethylation; Microwave irradiation; Green chemistry;100%
...Expand
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

tetrakis(acetonitrile)palladium(II) tetrafluoroborate
21797-13-7

tetrakis(acetonitrile)palladium(II) tetrafluoroborate

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

N,N’-di(3-pyridyl)-1,4,5,8-naphthalenetetracarboxydiimide
6016-04-2

N,N’-di(3-pyridyl)-1,4,5,8-naphthalenetetracarboxydiimide

2C57H39N9O3*6Pd(2+)*12BF4(1-)*3C24H12N4O4

2C57H39N9O3*6Pd(2+)*12BF4(1-)*3C24H12N4O4

Conditions
ConditionsYield
In chloroform; acetonitrile at 60℃; for 20h;100%
...Expand
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

C61H49NOP4

C61H49NOP4

Conditions
ConditionsYield
With dichloromethane; triethylamine for 24h; Inert atmosphere;99.9%
benzaldehyde
100-52-7

benzaldehyde

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

4,4′-bis(benzylideneamino)diphenyl ether
7203-56-7

4,4′-bis(benzylideneamino)diphenyl ether

Conditions
ConditionsYield
With acetic acid In toluene for 2h; Reflux; Dean-Stark;99%
In ethanol Heating;69%
In ethanol Heating;
salicylaldehyde
90-02-8

salicylaldehyde

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

2,2'-[oxybis(4,1-phenylenenitrilomethylylidene)]diphenol
7107-96-2

2,2'-[oxybis(4,1-phenylenenitrilomethylylidene)]diphenol

Conditions
ConditionsYield
With acetic acid In toluene for 2h; Dean-Stark; Reflux;99%
In ethanol at 78℃; for 3h;96%
In ethanol for 6h; Reflux;92%
With sodium acetate In methanol at 70℃; for 1h;90%
In ethanol for 1h; Heating;
3,3',4,4'-biphenyltetracarboxylic anhydride
2420-87-3

3,3',4,4'-biphenyltetracarboxylic anhydride

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer; monomer(s): 3,4,3\,,4\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

polymer; monomer(s): 3,4,3\,,4\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

Conditions
ConditionsYield
99%
formaldehyd
50-00-0

formaldehyd

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

bis[4-(1,3,5-dithiazinan-5-yl)phenyl]oxide

bis[4-(1,3,5-dithiazinan-5-yl)phenyl]oxide

Conditions
ConditionsYield
With hydrogen sulfide In chloroform at 20 - 40℃; for 3.5h;99%
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

tetrakis(acetonitrile)palladium(II) tetrafluoroborate
21797-13-7

tetrakis(acetonitrile)palladium(II) tetrafluoroborate

tris(3-pyridyl)-1,3,5-benzene

tris(3-pyridyl)-1,3,5-benzene

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

C78H54N12O3Pd3(6+)*6BF4(1-)

C78H54N12O3Pd3(6+)*6BF4(1-)

Conditions
ConditionsYield
Stage #1: 2,6-Pyridinedicarboxaldehyde; tetrakis(acetonitrile)palladium(II) tetrafluoroborate; 4,4'-oxydiphenylene diamine In acetonitrile at 60℃; for 20h;
Stage #2: tris(3-pyridyl)-1,3,5-benzene In acetonitrile at 60℃; for 2h;		99%
...Expand
1,5-bis(benzaldehydeoxy)-3-oxopentane
82645-24-7

1,5-bis(benzaldehydeoxy)-3-oxopentane

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

2,7,10,13-tetraoxa-4,16-diaza-1,3(1,4),6,14(1,2)-tetrabenzenacyclohexadecaphane-4,15-diene

2,7,10,13-tetraoxa-4,16-diaza-1,3(1,4),6,14(1,2)-tetrabenzenacyclohexadecaphane-4,15-diene

Conditions
ConditionsYield
In dichloromethane at 20℃; for 264h;99%
acetic anhydride
108-24-7

acetic anhydride

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

N-[4-(4-acetylaminophenoxy)phenyl]acetamide
3070-86-8

N-[4-(4-acetylaminophenoxy)phenyl]acetamide

Conditions
ConditionsYield
In acetone at 0℃;98%
With triethylamine In acetone at 0℃; for 2h;98%
In chlorobenzene at 90 - 95℃; for 2h;93%
In acetic acid for 2h; Ambient temperature;77.4%
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

3,3'-[4,4'-thiobis(phenylenethio)]bis(2,4-dichlorophenyl propionate)

3,3'-[4,4'-thiobis(phenylenethio)]bis(2,4-dichlorophenyl propionate)

polymer, ordered poly(amide-thioether), Mn 19000, Mw 36000; monomer(s): 3,3-[4,4-thiobis(phenylenethio)]bis(2,4-dichlorophenyl propionate); 4,4-oxydianiline

polymer, ordered poly(amide-thioether), Mn 19000, Mw 36000; monomer(s): 3,3-[4,4-thiobis(phenylenethio)]bis(2,4-dichlorophenyl propionate); 4,4-oxydianiline

Conditions
ConditionsYield
With benzotriazol-1-ol In 1-methyl-pyrrolidin-2-one at 80℃; for 48h;98%
1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

N-phenyl-4-(4-anilinophenoxy)aniline

N-phenyl-4-(4-anilinophenoxy)aniline

Conditions
ConditionsYield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;98%
2,3',3,4'-biphenyltetracarboxylic acid dianhydride
36978-41-3

2,3',3,4'-biphenyltetracarboxylic acid dianhydride

2,3,2',3'-biphenyltetracarboxylic dianhydride
3711-04-4

2,3,2',3'-biphenyltetracarboxylic dianhydride

3,3',4,4'-biphenyltetracarboxylic anhydride
2420-87-3

3,3',4,4'-biphenyltetracarboxylic anhydride

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer; monomer(s): 2,3,3\,,4\-biphenyltetracarboxylic dianhydride; 2,3,2\,,3\-biphenyltetracarboxylic dianhydride; 3,4,3\,,4\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

polymer; monomer(s): 2,3,3\,,4\-biphenyltetracarboxylic dianhydride; 2,3,2\,,3\-biphenyltetracarboxylic dianhydride; 3,4,3\,,4\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

Conditions
ConditionsYield
98%
...Expand
2,3',3,4'-biphenyltetracarboxylic acid dianhydride
36978-41-3

2,3',3,4'-biphenyltetracarboxylic acid dianhydride

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer; monomer(s): 2,3,3\,,4\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

polymer; monomer(s): 2,3,3\,,4\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

Conditions
ConditionsYield
98%
3,3'-bis(N-aminophthalimide)
916066-54-1

3,3'-bis(N-aminophthalimide)

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid
2421-28-5

dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid

polymer, Mn/Mw = 1.6, Mn = 51210 g/mol, Mw = 82240 g/mol, inherent viscosity = 0.50 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 4,4\-oxydianiline; 3,3\44,4\-biphenyltetracarboxylic acid dianhydride

polymer, Mn/Mw = 1.6, Mn = 51210 g/mol, Mw = 82240 g/mol, inherent viscosity = 0.50 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 4,4\-oxydianiline; 3,3\44,4\-biphenyltetracarboxylic acid dianhydride

Conditions
ConditionsYield
With 4-chloro-phenol; benzoic acid at 100 - 190℃;98%
...Expand
3-acetyl-2-oxo-4,5-dihydrofuran
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

C24H24N2O5

C24H24N2O5

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 12h; Heating;98%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

4,4'-bis(1-naphthylmethylideneamino)diphenyl ether
387850-01-3

4,4'-bis(1-naphthylmethylideneamino)diphenyl ether

Conditions
ConditionsYield
With acetic acid In toluene for 2h; Inert atmosphere; Reflux; Dean-Stark;98%
3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

6,6′-((1E,1′E)-((oxybis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(2-methoxyphenol)

6,6′-((1E,1′E)-((oxybis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(2-methoxyphenol)

Conditions
ConditionsYield
In ethanol for 3.5h; Reflux; Schlenk technique; Inert atmosphere;98%
In methanol at 40℃; for 6h;80%
In methanol at 40℃; for 6h;80%
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

trans-4-[60]fullerenobisacetic acid

trans-4-[60]fullerenobisacetic acid

Polymer; Monomer(s): trans-4-[60]fullerenobisacetic acid; 4,4-oxydianiline;

Polymer; Monomer(s): trans-4-[60]fullerenobisacetic acid; 4,4-oxydianiline;

Conditions
ConditionsYield
With pyridine; triphenyl phosphite; lithium chloride; 1-methyl-pyrrolidin-2-one at 115℃; for 96h;97%
4,4'-dimercaptodiphenyl sulfide
19362-77-7

4,4'-dimercaptodiphenyl sulfide

2,4-dichlorophenoxy acrylate
4513-42-2

2,4-dichlorophenoxy acrylate

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer, ordered poly(amide-thioether), Mn 25000, Mw 44000; monomer(s): 2,4-dichlorophenyl acrylate; 4,4\-thiobis(benzenethiol); 4,4\-oxydianiline

polymer, ordered poly(amide-thioether), Mn 25000, Mw 44000; monomer(s): 2,4-dichlorophenyl acrylate; 4,4\-thiobis(benzenethiol); 4,4\-oxydianiline

Conditions
ConditionsYield
With TEA; benzotriazol-1-ol In 1-methyl-pyrrolidin-2-one at 20 - 80℃; for 50h;97%
...Expand
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

bis(5-carboxy-1,3-phenylene)-20-crown-6
198328-20-0

bis(5-carboxy-1,3-phenylene)-20-crown-6

polymer, Mn 12.9 kg/mol by GPC, Mw/Mn 4.28; monomer(s): bis(5-carboxy-1,3-phenylene)-20-crown-6; 4,4\-oxydianiline

polymer, Mn 12.9 kg/mol by GPC, Mw/Mn 4.28; monomer(s): bis(5-carboxy-1,3-phenylene)-20-crown-6; 4,4\-oxydianiline

Conditions
ConditionsYield
With pyridine; triphenyl phosphite; lithium chloride In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;97%
2,3,2',3'-biphenyltetracarboxylic dianhydride
3711-04-4

2,3,2',3'-biphenyltetracarboxylic dianhydride

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

polymer; monomer(s): 2,3,2\,,3\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

polymer; monomer(s): 2,3,2\,,3\-biphenyltetracarboxylic dianhydride; 4,4\-oxydianiline

Conditions
ConditionsYield
97%
C15H15NO6

C15H15NO6

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

C26H23N3O6

C26H23N3O6

Conditions
ConditionsYield
With 5,15,10,20-tetraphenylporphyrin; calcium chloride In pyridine; 1-methyl-pyrrolidin-2-one at 60 - 130℃; for 10.5h; Inert atmosphere;97%
bis(phenyl) carbonate
102-09-0

bis(phenyl) carbonate

4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

4,4'-oxydiphenylene bis-phenylcarbamate
21649-32-1

4,4'-oxydiphenylene bis-phenylcarbamate

Conditions
ConditionsYield
With isobutyric Acid; 1,3,5-tris(N,N-dimethylaminopropyl)-hexahydro-s-triazine In toluene at 55℃; for 48h;97%
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

1-azido-4-(4-azidophenoxy)benzene
48180-65-0

1-azido-4-(4-azidophenoxy)benzene

Conditions
ConditionsYield
Stage #1: 4,4'-oxydiphenylene diamine With toluene-4-sulfonic acid In water for 0.0166667h;
Stage #2: With sodium nitrite In water
Stage #3: With sodium azide In water		96%
Stage #1: 4,4'-oxydiphenylene diamine With 1-methyl-2-oxopyrrolidinium hydrogen sulfate In water at 20℃; for 0.0166667h; Grinding;
Stage #2: With sodium nitrite In water at 20℃; Grinding;
Stage #3: With sodium azide In water at 20℃; Grinding;		94%
Stage #1: 4,4'-oxydiphenylene diamine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.25h;
Stage #2: With sodium azide In water at 0℃;		90%

4,4'-Oxydianiline Chemical Properties

Molecular structure of 4,4'-Oxydianiline (CAS NO.101-80-4) is:

Product Name: 4,4'-Oxydianiline
CAS Registry Number: 101-80-4
IUPAC Name: 4-(4-Aminophenoxy)aniline
Molecular Weight: 200.23648 [g/mol]
Molecular Formula: C12H12N2O
XLogP3: 1.4
H-Bond Donor: 2
H-Bond Acceptor: 3 
EINECS: 202-977-0
Melting Point: 188-192 °C(lit.)
Surface Tension: 55.9 dyne/cm
Density: 1.216 g/cm3
Flash Point: 218.9 °C
Enthalpy of Vaporization: 63.87 kJ/mol
Boiling Point: 389.4 °C at 760 mmHg
Vapour Pressure: 2.87E-06 mmHg at 25 °C
Water Solubility: Insoluble. <0.01 g/100 mL at 15 °C
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. Hygroscopic.
Product Categories: Intermediates of Dyes and Pigments; Biphenyl & Diphenyl ether; Diphenyl Ethers (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; Monomer for Polyimide film

4,4'-Oxydianiline Uses

4,4'-Oxydianiline (CAS NO.101-80-4) is used as the monomer of polyimide,which is high temperature resistant polymer material. It can be used in the production of a wide variety of polymer resins. It is also used in the production of a wide variety of polymer resins and plastic industry.

4,4'-Oxydianiline Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 650mg/kg (650mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 43, 1982.
mouse LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
mouse LD50 oral 685mg/kg (685mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rabbit LD50 intraperitoneal 650mg/kg (650mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rabbit LD50 oral 700mg/kg (700mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rat LD50 intraperitoneal 365mg/kg (365mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rat LD50 oral 725mg/kg (725mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.

4,4'-Oxydianiline Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 ,1982,p. 203.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 16 ,1978,p. 301.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-205 ,1980. . Reported in EPA TSCA Inventory.

4,4'-Oxydianiline Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ToxicT, DangerousN
Risk Statements: 45-46-23/24/25-51/53-62-36/37/38-22 
R45:May cause cancer. 
R46:May cause heritable genetic damage. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R62:Risk of impaired fertility. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R22:Harmful if swallowed.
Safety Statements: 53-45-61-36/37-26-20 
S53:Avoid exposure - obtain special instructions before use. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36/37:Wear suitable protective clothing and gloves. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S20:When using, do not eat or drink.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: BY7900000
HazardClass: 6.1
PackingGroup: III
HS Code: 29222900

4,4'-Oxydianiline Standards and Recommendations

DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

4,4'-Oxydianiline Specification

 4,4'-Oxydianiline , its cas register number is 101-80-4. It also can be called Bis(4-aminophenyl) ether ; Di-(4-aminophenyl)ether ; 4,4'-Diaminobiphenyl oxide ; 4,4'-Diaminodiphenyl ether ; 4,4'-Diaminodiphenyl oxide ; 4,4'-Diaminophenyl ether ; 4,4'-Diaminophenyl oxide ; 4,4'-Oxybisaniline ; 4,4'-Oxybisbenzenamine ; 4,4'-Oxydiphenylamine ; 4,4-Diaminodiphenyl ether ; 4-13-00-01038 (Beilstein Handbook Reference) ; 4-Aminophenyl ether ; AI3-18375 ; Aniline, 4,4'-oxydi- ; BRN 0475735 ; Bis(4-aminophenyl) ether ; Bis(4-aminophenyl)ether ; Bis(p-aminophenyl) ether ; Bis(p-aminophenyl)ether ; CCRIS 491 ; Dadpe ; Diaminodiphenyl ether ; Ether, 4,4'-diaminodiphenyl ; HSDB 1316 ; NCI-C50146 ; NSC 37075 ; Oxybis(4-aminobenzene) ; Oxydi-p-phenylenediamine ; Oxydianiline ; p,p'-Diaminodiphenyl ether ; p,p'-Oxybis(aniline) ; p,p'-Oxydianiline ; p-Aminophenyl ether ; Aniline, 4,4'-oxydi- ; Benzenamine, 4,4'-oxybis- . It is a odorless colorless crystals or an odorless fine, beige powder.  It is an ether derivative of aniline. also it is a useful monomer and cross-linking agent for polymers.

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