Product Name

  • Name

    3,4'-Oxydianiline

  • EINECS 220-190-0
  • CAS No. 2657-87-6
  • Article Data9
  • CAS DataBase
  • Density 1.216 g/cm3
  • Solubility
  • Melting Point 67-71 °C(lit.)
  • Formula C12H12N2O
  • Boiling Point 384.7 °C at 760 mmHg
  • Molecular Weight 200.24
  • Flash Point 209.9 °C
  • Transport Information
  • Appearance light brown powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2657-87-6 (3,4'-Oxydianiline)
  • Hazard Symbols IrritantXi
  • Synonyms 3,4'-DAPE;3,4'-Diaminodiphenyl ether;3,4'-Oxydiphenylamine;3-Aminophenyl 4-aminophenyl ether;4,3'-Diaminodiphenyl oxide;
  • PSA 61.27000
  • LogP 3.80570

Synthetic route

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
Stage #1: 4-chlorobenzonitrile; m-Hydroxyaniline With potassium carbonate; sodium hydrogensulfite In N,N-dimethyl-formamide at 100 - 120℃; for 10h; Inert atmosphere;
Stage #2: With iron(III) chloride; 5%-palladium/activated carbon; hydrogen at 60 - 80℃; under 3750.38 Torr; for 2h; Autoclave;
96.1%
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;54%
1-nitro-3-(4-nitrophenoxy)benzene
2914-72-9

1-nitro-3-(4-nitrophenoxy)benzene

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
With hydrogenchloride; tin
4-(3-nitrophenoxy)phenylamine
60732-27-6

4-(3-nitrophenoxy)phenylamine

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
With hydrazine
potassium 4-nitrophenolate
1124-31-8

potassium 4-nitrophenolate

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper-powder / 150 °C
2: tin; aqueous hydrochloric acid
View Scheme
4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper-powder / 150 °C
2: tin; aqueous hydrochloric acid
View Scheme
3-amino-cyclohex-2-enone
5220-49-5

3-amino-cyclohex-2-enone

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

3-amino-4'-nitrodiphenyl ether
22528-34-3

3-amino-4'-nitrodiphenyl ether

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
With 0.5% Pd on alumina; hydrogen In N,N-dimethyl-formamide at 30℃; for 7h; Green chemistry;> 99.9 %Spectr.
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

epichlorohydrin
106-89-8

epichlorohydrin

N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether
129998-27-2

N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 80℃; for 15h;100%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

indole-2,3-dione
91-56-5

indole-2,3-dione

3,3'-[oxybis[(3,1)-(4',1')phenylenenitrilo]]bis[1,3-dihydro-2H-indol-2-one]

3,3'-[oxybis[(3,1)-(4',1')phenylenenitrilo]]bis[1,3-dihydro-2H-indol-2-one]

Conditions
ConditionsYield
With acetic acid In ethanol for 28h; Heating;91%
In water at 20℃; for 45h;80%
In ethanol Heating;
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

(E)-N-(anthracen-10-ylmethylene)-3-(4-[(E)-anthracen-10-ylmethyleneamino]phenoxy)benzeneamine
1251936-16-9

(E)-N-(anthracen-10-ylmethylene)-3-(4-[(E)-anthracen-10-ylmethyleneamino]phenoxy)benzeneamine

Conditions
ConditionsYield
In ethanol Reflux;88%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

N,N'-bis-Boc-S-methyl-isothiourea
322474-21-5

N,N'-bis-Boc-S-methyl-isothiourea

3,4’-bis[2,3-di(tert-butoxycarbonyl)guanidino]diphenylether

3,4’-bis[2,3-di(tert-butoxycarbonyl)guanidino]diphenylether

Conditions
ConditionsYield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃;87%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride
1107-00-2

4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride

2-(4'-aminophenyl)ethyl alcohol
104-10-9

2-(4'-aminophenyl)ethyl alcohol

linear fluorine-containing hydroxy-terminated polyimide

linear fluorine-containing hydroxy-terminated polyimide

Conditions
ConditionsYield
Stage #1: 3,4'-diaminodiphenyl ether; 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride; 2-(4'-aminophenyl)ethyl alcohol In 1-methyl-pyrrolidin-2-one at 20℃; for 12h;
Stage #2: In para-xylene at 180℃; for 6h; Further stages.;
83%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

2,3',4,5',6-pentabromo-3,4'-diaminodiphenyl ether

2,3',4,5',6-pentabromo-3,4'-diaminodiphenyl ether

Conditions
ConditionsYield
With bromine In acetic acid at 35℃; for 1h;81%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate
145013-05-4

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

3-amino-{4'-[2,3-di(tert-butoxycarbonyl)]guanidino}diphenyl ether

3-amino-{4'-[2,3-di(tert-butoxycarbonyl)]guanidino}diphenyl ether

Conditions
ConditionsYield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃;77%
With triethylamine; mercury dichloride In dichloromethane at 25℃; for 12h;51%
N-tert-butoxycarbonyl-N’-phenylthiourea
1037587-67-9

N-tert-butoxycarbonyl-N’-phenylthiourea

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

3-amino-4'-[2-(tert-butoxycarbonyl)-3-phenylguanidino]diphenyl ether

3-amino-4'-[2-(tert-butoxycarbonyl)-3-phenylguanidino]diphenyl ether

Conditions
ConditionsYield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃; for 4h;76%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

3-nitro-4-chloro-1,8-naphthalene dicarboxylic acid anhydride
52871-22-4

3-nitro-4-chloro-1,8-naphthalene dicarboxylic acid anhydride

C36H18N4O11

C36H18N4O11

Conditions
ConditionsYield
In ethanol; N,N-dimethyl-formamide for 0.5h; Heating;75%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate
145013-05-4

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

A

3-amino-{4'-[2,3-di(tert-butoxycarbonyl)]guanidino}diphenyl ether

3-amino-{4'-[2,3-di(tert-butoxycarbonyl)]guanidino}diphenyl ether

B

C23H30N4O5

C23H30N4O5

Conditions
ConditionsYield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃;A 75%
B 25%
2-(3,5-dinitrobenzamido)acetic acid
16533-70-3

2-(3,5-dinitrobenzamido)acetic acid

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

C30H22N8O13
1037570-01-6

C30H22N8O13

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;70%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

benzoyl chloride
98-88-4

benzoyl chloride

C26H20N2O3
1037569-97-3

C26H20N2O3

Conditions
ConditionsYield
With (+/-)-propylene oxide In tetrahydrofuran at 20℃;70%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

-glycin
52071-01-9

-glycin

C40H44N6O13
1037570-05-0

C40H44N6O13

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;69%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

hippuroyl-Gly-Gly
31384-90-4

hippuroyl-Gly-Gly

C38H38N8O9
1037570-06-1

C38H38N8O9

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;68%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

3,5-dinitrobenoyl chloride
99-33-2

3,5-dinitrobenoyl chloride

C26H16N6O11
1037569-98-4

C26H16N6O11

Conditions
ConditionsYield
With (+/-)-propylene oxide In tetrahydrofuran at 20℃;68%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester
173300-83-9

2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester

3,4’-bis[2,3-di(tert-butoxycarbonyl)-2-iminoimidazolidino]diphenyl ether

3,4’-bis[2,3-di(tert-butoxycarbonyl)-2-iminoimidazolidino]diphenyl ether

Conditions
ConditionsYield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃;68%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

N-(4-chloro-3-trifluoromethylphenyl)-N’-(tert-butoxycarbonyl)thiourea

N-(4-chloro-3-trifluoromethylphenyl)-N’-(tert-butoxycarbonyl)thiourea

3-amino-4'-[2-(tert-butoxycarbonyl)-3-(4-chloro-3-trifluoromethyl)guanidino]diphenyl ether

3-amino-4'-[2-(tert-butoxycarbonyl)-3-(4-chloro-3-trifluoromethyl)guanidino]diphenyl ether

Conditions
ConditionsYield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃; for 4h;68%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

2-hydroxy-3-(morpholinomethyl)benzaldehyde

2-hydroxy-3-(morpholinomethyl)benzaldehyde

2-((3-(4-(2-hydroxy-3-(morpholinomethyl)benzylideneamino)phenoxy)phenylimino)methyl)-6-(morpholinomethyl)phenol

2-((3-(4-(2-hydroxy-3-(morpholinomethyl)benzylideneamino)phenoxy)phenylimino)methyl)-6-(morpholinomethyl)phenol

Conditions
ConditionsYield
In ethanol Reflux;68%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine
1037569-82-6

N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine

C34H28N10O15
1037570-04-9

C34H28N10O15

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;66%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

6-(4-aminophenoxy)-3-hydroxy-3-(trifluoromethyl)indolin-2-one
1400992-23-5

6-(4-aminophenoxy)-3-hydroxy-3-(trifluoromethyl)indolin-2-one

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 20 - 150℃; for 0.416667h; Microwave irradiation;66%
N-(N'-benzoyl-2-aminoethanoyl)-2-aminoethanoic acid
1145-32-0

N-(N'-benzoyl-2-aminoethanoyl)-2-aminoethanoic acid

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

C34H32N6O7
1037570-03-8

C34H32N6O7

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;65%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

N-(3,5-dinitro-benzoyl)-glycyl=>glycyl=>glycine
1037569-83-7

N-(3,5-dinitro-benzoyl)-glycyl=>glycyl=>glycine

C38H34N12O17
1037570-07-2

C38H34N12O17

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;65%
Hippuric Acid
495-69-2

Hippuric Acid

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

C30H26N4O5
1037570-00-5

C30H26N4O5

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;64%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

C32H32N2O9
1037569-99-5

C32H32N2O9

Conditions
ConditionsYield
With (+/-)-propylene oxide In tetrahydrofuran at 20℃;64%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

(3,4,5-trimethoxybenzoylamino)acetic acid
40915-27-3

(3,4,5-trimethoxybenzoylamino)acetic acid

C36H38N4O11
1037570-02-7

C36H38N4O11

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;63%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

-glycin
52071-02-0

-glycin

C44H50N8O15
1037570-08-3

C44H50N8O15

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;61%
[2-(cyclohexanecarbonylamino)acetylamino]acetic acid
1037569-77-9

[2-(cyclohexanecarbonylamino)acetylamino]acetic acid

3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

C34H44N6O7
1037569-78-0

C34H44N6O7

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;58%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine
1037569-82-6

N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine

C23H20N6O8
1037569-79-1

C23H20N6O8

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 15h;56%
3,4'-diaminodiphenyl ether
2657-87-6

3,4'-diaminodiphenyl ether

5-[(3,4,5-trimethoxybenzoyl)amino]pentanoic acid
32407-06-0

5-[(3,4,5-trimethoxybenzoyl)amino]pentanoic acid

C42H50N4O11
1037569-76-8

C42H50N4O11

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;55%

3,4'-Oxydianiline Chemical Properties

Product Name: 3,4'-Oxydianiline (CAS NO.2657-87-6)

Molecular Formula: C12H12N2O
Molecular Weight: 200.24g/mol
Mol File: 2657-87-6.mol
EINECS: 220-190-0
Melting Point: 67-71 °C(lit.)
Boiling point: 384.7 °C at 760 mmHg
Flash Point: 209.9 °C
Density: 1.216 g/cm3
Index of Refraction: 1.665 
Molar Refractivity: 61.16 cm3 
Molar Volume: 164.5 cm3 
Surface Tension: 55.9 dyne/cm
Enthalpy of Vaporization: 63.34 kJ/mol
Vapour Pressure: 4E-06 mmHg at 25°C
XLogP3-AA: 2.2
H-Bond Donor: 2
H-Bond Acceptor: 3
Structure Descriptors of 3,4'-Oxydianiline (CAS NO.2657-87-6):
  IUPAC Name: 3-(4-aminophenoxy)aniline
  Canonical SMILES: C1=CC(=CC(=C1)OC2=CC=C(C=C2)N)N
  InChI: InChI=1S/C12H12N2O/c13-9-4-6-11(7-5-9)15-12-3-1-2-10(14)8-12/h1-8H,13-14H2 
  InChIKey: ZBMISJGHVWNWTE-UHFFFAOYSA-N
Product Categories: Biphenyl & Diphenyl ether; Amines; Miscellaneous; Diphenyl Ethers (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; Amine Monomers; Monomers; Primary Amines

3,4'-Oxydianiline Safety Profile

Safety Information of 3,4'-Oxydianiline (CAS NO.2657-87-6):
Hazard Codes: XiIrritant
Risk Statements: 36/37/38  
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3

3,4'-Oxydianiline Specification

 3,4'-Oxydianiline , its CAS NO. is 2657-87-6, the synonyms are 3-(4-Aminophenoxy)aniline ; 3-(4-Aminophenoxy)phenylamine ; 3-Aminophenyl 4-aminophenyl ether ; Benzenamine, 3-(4-aminophenoxy)- .

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