N-(4-Aminophenyl)-1,4-benzenediamine supplier

Name
4,4'-Iminodianiline
EINECS 208-673-4
CAS No. 537-65-5
Article Data30
CAS DataBase
Density 1.245g/cm³
Solubility
Melting Point 158°C
Formula C12H13 N3
Boiling Point 410.7°Cat760mmHg
Molecular Weight 199.255
Flash Point 239.2°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,4-Benzenediamine,N-(4-aminophenyl)- (9CI); Diphenylamine, 4,4'-diamino- (6CI,7CI,8CI);4,4'-Diaminodiphenylamine; 4,4'-Iminodianiline; Benzenamine, 4,4'-iminobis-;Bis(4-aminophenyl)amine; Bis(p-aminophenyl)amine; C.I. 76120;Di(p-aminophenyl)amine; Diazol Black C; Indamine;N-(4-Aminophenyl)-1,4-benzenediamine; N-(4-Aminophenyl)-p-phenylenediamine; NSC33417; p,p'-Diaminodiphenylamine; p,p'-Iminodianiline
PSA 147.05000
LogP 4.25800

Synthetic route

: 6149-34-4
N-(4-nitrophenyl)-1,4-phenylenediamine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With hydrogen; nickel In ethanol at 60℃; under 30003 Torr; for 2h; Reagent/catalyst; Temperature; Autoclave;	93.2%
With tin(II)chloride dihydrate; ethanol at 70℃; for 1h; Inert atmosphere;

: 1821-27-8
N,N-bis(p-nitrophenyl)amine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With acetic acid; zinc
With hydrogenchloride; tin
With sodium sulfide at 140 - 150℃;

: 3313-75-5
Bis-(4-nitro-phenyl)-oxy-aminyl

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

: N,N-bis-(4-nitro-phenyl)-formamide

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With iron

: 106038-75-9
N-acetyl-4,4'-dinitrodiphenylamine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With iron

: 142-04-1
aniline hydrochloride

: 540-24-9
p-phenylenediamine hydrochloride

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With potassium dichromate und anschliessenden Reduktion des Oxydationsprodukts (Indamin) mit Zink und Salzsaeure in der Waerme;

: 142-04-1
aniline hydrochloride

: 60-09-3
aniline yellow

: 62-53-3
aniline

: 537-65-5
4,4'-diaminodiphenylamine

...Expand

: 540-24-9
p-phenylenediamine hydrochloride

: 106-50-3
1,4-phenylenediamine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With water at 200℃;

: 4128-71-6
N-[4-(phenylazo)phenyl]-acetamide

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With hydrochloride of tin dichloride

: 142-04-1
aniline hydrochloride

: 62-53-3
aniline

hydrochloride of p-amino-azobenzene: hydrochloride of p-amino-azobenzene

: 537-65-5
4,4'-diaminodiphenylamine

...Expand

: 7732-18-5
water

: 106-50-3
1,4-phenylenediamine

hydrochloride of/the/ p-phenylenediamine: hydrochloride of/the/ p-phenylenediamine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
at 200℃;

...Expand

: 62-53-3
aniline

: 106-50-3
1,4-phenylenediamine

potassium dichromate: potassium dichromate

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
anschl. mit Zink-Staub und HCl;
und Behandeln mit Zinkstaub und Salzsaeure;

...Expand

: 7664-93-9
sulfuric acid

: 60-09-3
aniline yellow

zinc: zinc

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
dann mit verd. Schwefelsaeure;

...Expand

aniline black: aniline black

A: 537-65-5
4,4'-diaminodiphenylamine

B: 106-50-3
1,4-phenylenediamine

Conditions

Conditions	Yield
With hydrogenchloride; tin
With phosphorus; hydrogen iodide

: 7647-01-0
hydrogenchloride

: 4128-71-6
N-[4-(phenylazo)phenyl]-acetamide

tin dichloride: tin dichloride

A: 537-65-5
4,4'-diaminodiphenylamine

B: 108272-17-9
N-acetyl-4,4'-diaminodiphenylamine

C: 62-53-3
aniline

D: 106-50-3
1,4-phenylenediamine

...Expand

4-amino-azobenzene hydrochloride: 4-amino-azobenzene hydrochloride

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With sulfuric acid; sulfur dioxide; zinc

5-amino-2-<4-amino-anilino>-benzene-sulfonic acid-(1): 5-amino-2-<4-amino-anilino>-benzene-sulfonic acid-(1)

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With sulfuric acid

: 7647-01-0
hydrogenchloride

: 64-17-5
ethanol

: 3313-75-5
Bis-(4-nitro-phenyl)-oxy-aminyl

tin (II)-chloride: tin (II)-chloride

: 537-65-5
4,4'-diaminodiphenylamine

...Expand

: 7647-01-0
hydrogenchloride

: 108272-17-9
N-acetyl-4,4'-diaminodiphenylamine

: 537-65-5
4,4'-diaminodiphenylamine

: 7664-93-9
sulfuric acid

: 17867-12-8
bis-(4-benzylidenamino-phenyl)-amine

A: 537-65-5
4,4'-diaminodiphenylamine

B: 100-52-7
benzaldehyde

...Expand

: 60-29-7
diethyl ether

: 861362-54-1
N,N-bis-(4-nitro-phenyl)-o-trityl-hydroxylamine

palladium black: palladium black

A: 76-84-6
triphenylmethyl alcohol

B: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 122-39-4
diphenylamine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; glacial acetic acid; isopentyl nitrite; nitric acid / Man laesst 24 Stdn. stehen und behandelt das erhaltene, von der Mutterlauge getrennte, mit Alkohol und Aether gewaschene Reaktionsprodukt mit einem Gemisch gleicher Teile Alkohol und rauchender Salzsaeure 2: acetic acid; zinc View Scheme

: 712-51-6
Diphenylaminoxid-Radikal

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrogen dioxide; benzene; diethyl ether 2: tin (II)-chloride; aqueous alcoholic hydrochloric acid View Scheme

: phenylmagnesium bromide

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether 2: nitrogen dioxide; benzene; diethyl ether 3: tin (II)-chloride; aqueous alcoholic hydrochloric acid View Scheme

: 586-96-9
Nitrosobenzene

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether 2: nitrogen dioxide; benzene; diethyl ether 3: tin (II)-chloride; aqueous alcoholic hydrochloric acid View Scheme

: 106-50-3
1,4-phenylenediamine

: 17082-12-1
trans-azobenzene

: 537-65-5
4,4'-diaminodiphenylamine

: 100-01-6
4-nitro-aniline

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / ethyl methyl ether / 7 h / Inert atmosphere; Reflux 2: tin(II)chloride dihydrate; ethanol / 1 h / 70 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / dimethyl sulfoxide / 12 h / 80 °C 2: hydrogenchloride; tin / water / 18 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / dimethyl sulfoxide / 12 h / 80 °C 2.1: hydrogenchloride; tin / water / 18 h / Reflux; Inert atmosphere 2.2: pH 12 / Inert atmosphere View Scheme

: 350-46-9
4-Fluoronitrobenzene

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / ethyl methyl ether / 7 h / Inert atmosphere; Reflux 2: tin(II)chloride dihydrate; ethanol / 1 h / 70 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium acetate / ethyl methyl ether / 7 h / Inert atmosphere; Reflux 2: tin(II)chloride dihydrate; ethanol / 1 h / 70 °C / Inert atmosphere View Scheme

: 106-50-3
1,4-phenylenediamine

: 537-65-5
4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / ethyl methyl ether / 7 h / Inert atmosphere; Reflux 2: tin(II)chloride dihydrate; ethanol / 1 h / 70 °C / Inert atmosphere View Scheme

: 537-65-5
4,4'-diaminodiphenylamine

: 70-34-8
2,4-Dinitrofluorobenzene

: N,N'-bis(2'',4''-dinitrophenyl)-4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 30℃; under 11250900 Torr; for 72h;	100%

: 537-65-5
4,4'-diaminodiphenylamine

: 350-46-9
4-Fluoronitrobenzene

: 258269-00-0
N,N’’-bis(4’’-nitrophenyl)-4,4’-diaminodiphenylamine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40℃; under 11250900 Torr; for 72h;	98.6%
With triethylamine In dimethyl sulfoxide	88%
With triethylamine In dimethyl sulfoxide at 90℃; for 72h; Inert atmosphere;	87%

: 537-65-5
4,4'-diaminodiphenylamine

: 1493-27-2
ortho-nitrofluorobenzene

: N,N'-bis(2''-nitrophenyl)-4,4'-diaminodiphenylamine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40℃; under 11250900 Torr; for 72h;	97.5%

: 2-chloro-4,6-bis-((2,2,6,6-tetramethyl-piperidin-4-yl)butylamino)-1,3,5-triazine

: 537-65-5
4,4'-diaminodiphenylamine

: C70H119N17

Conditions

Conditions	Yield
Stage #1: 2-chloro-4,6-bis-((2,2,6,6-tetramethyl-piperidin-4-yl)butylamino)-1,3,5-triazine; 4,4'-diaminodiphenylamine In toluene at 85℃; for 5.5h; Stage #2: With sodium hydroxide In toluene at 115℃; for 7h; Solvent; Temperature; Time;	95.2%

: 537-65-5
4,4'-diaminodiphenylamine

: 555-16-8
4-nitrobenzaldehdye

: 52167-06-3
4-[(E)-(4-nitrophenyl)methyleneamino]-N-[4-[(E)-(4-nitrophenyl)methyleneamino]phenyl]aniline

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃; for 14h;	95%
With toluene-4-sulfonic acid In ethanol at 20℃;	95%
With ethanol

: 537-65-5
4,4'-diaminodiphenylamine

: 3-bromo-9-(tertbutyldimethylsilyl)-9H-carbazole

: TBSCz5

Conditions

Conditions	Yield
With di(tertbutyl)phenylphosphine; potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0) In toluene at 90℃; for 2.5h; Inert atmosphere;	95%
With di(tertbutyl)phenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 90℃; for 2.5h; Inert atmosphere;	95%

: 463-71-8
thiophosgene

: 537-65-5
4,4'-diaminodiphenylamine

: 1048037-23-5
bis(4-isothiocyanatophenyl)amine

Conditions

Conditions	Yield
In ethanol; water	86%

: 537-65-5
4,4'-diaminodiphenylamine

: 123-11-5
4-methoxy-benzaldehyde

: 4-[(E)-(4-methoxyphenyl)methyleneamino]-N-[4-[(E)-(4-methoxyphenyl)methylene-amino]phenyl]aniline

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃;	84%

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 537-65-5
4,4'-diaminodiphenylamine

: C102H68N8

Conditions

Conditions	Yield
With di(tertbutyl)phenylphosphine; palladium diacetate; sodium t-butanolate In toluene at 90℃; for 6h; Inert atmosphere;	83%
With di(tertbutyl)phenylphosphine; acetic acid; sodium t-butanolate In toluene at 90℃; for 6h; Inert atmosphere;	83%
With di(tertbutyl)phenylphosphine; palladium diacetate In toluene at 90℃; for 6h; Inert atmosphere;

: 537-65-5
4,4'-diaminodiphenylamine

: tert-butyl (4'-bromo-[1,1'biphenyl]-4-yl)(phenyl)carbamate

: C127H118N8O10

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 50℃; for 26h; Inert atmosphere;	83%

: 537-65-5
4,4'-diaminodiphenylamine

: 7144-08-3
Cholesteryl chloroformate

: C68H101N3O4

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	83%

: 537-65-5
4,4'-diaminodiphenylamine

: 138310-84-6
N-(4-bromophenyl)-N-phenyl-1-naphthylamine

: C122H88N8

Conditions

Conditions	Yield
With di(tertbutyl)phenylphosphine; palladium diacetate; sodium t-butanolate In toluene at 100℃; for 3.5h; Inert atmosphere;	81%

: 3-bromo-9-benzyl-9H-carbazole

: 537-65-5
4,4'-diaminodiphenylamine

: N1,N1,N4-tris(9-benzyl-9H-carbazol-3-yl)-N4-(4-(bis(9-benzyl-9H-carbazol-3-yl)amino)phenyl) benzene-1,4-diamine

Conditions

Conditions	Yield
With di(tertbutyl)phenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 90℃; for 3h; Inert atmosphere;	80%

: 537-65-5
4,4'-diaminodiphenylamine

: 104-87-0
4-methyl-benzaldehyde

: 4-[(E)-p-tolylmethyleneamino]-N-[4-[(E)-p-tolylmethyleneamino]phenyl]aniline

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃;	80%

: 2033-24-1
cycl-isopropylidene malonate

: 537-65-5
4,4'-diaminodiphenylamine

: 149-73-5
trimethyl orthoformate

: C26H25N3O8

Conditions

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 1h; Reflux; Stage #2: 4,4'-diaminodiphenylamine for 2h; Reflux;	79%

...Expand

: 537-65-5
4,4'-diaminodiphenylamine

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

: 292634-05-0
4,4'-bis[1,3-di(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine

Conditions

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 0 - 20℃; Substitution;	76%

: 537-65-5
4,4'-diaminodiphenylamine

: 123-08-0
4-hydroxy-benzaldehyde

: 4-[(E)-[4-[4-[(E)-(4-hydroxyphenyl)methyleneamino]anilino]phenyl]iminomethyl]phenol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃;	75%

: 537-65-5
4,4'-diaminodiphenylamine

: 118-55-8
phenyl Salicylate

: C26H21N3O4

Conditions

Conditions	Yield
at 200℃; for 4h;	68.5%

: 537-65-5
4,4'-diaminodiphenylamine

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

: 4,4'-bis[2,3-di(tert-butoxycarbonyl)guanidino]diphenylamine

Conditions

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 0 - 20℃; Substitution;	66%

: 537-65-5
4,4'-diaminodiphenylamine

: 350-46-9
4-Fluoronitrobenzene

: N1-(4-aminophenyl)-N4-(4-nitrophenyl)-1,4-benzenediamine

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 90℃; for 72h; Inert atmosphere;	65.8%
With triethylamine In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	0.28 g

N-(4-Aminophenyl)-1,4-benzenediamine Chemical Properties

IUPAC Name: 1-N-(4-aminophenyl)benzene-1,4-diamine
Empirical Formula: C₁₂H₁₃N₃
Molecular Weight: 199.2517g/mol
EINECS: 208-673-4
Structure of 1,4-Benzenediamine,N1-(4-aminophenyl)- (CAS NO.537-65-5):

Index of Refraction: 1.733
Molar Refractivity: 64.09 cm³
Molar Volume: 160 cm³
Polarizability: 25.41×10^-24cm³
Surface Tension: 63.7 dyne/cm
Density: 1.245 g/cm³
Flash Point: 239.2 °C
Enthalpy of Vaporization: 66.31 kJ/mol
Boiling Point: 410.7 °C at 760 mmHg
Vapour Pressure: 5.89E-07 mmHg at 25°C
Canonical SMILES: C1=CC(=CC=C1N)NC2=CC=C(C=C2)N
InChI: InChI=1S/C12H13N3/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8,15H,13-14H2
InChIKey: QZHXKQKKEBXYRG-UHFFFAOYSA-N

N-(4-Aminophenyl)-1,4-benzenediamine Specification

1,4-Benzenediamine,N1-(4-aminophenyl)- , its cas register number is 537-65-5. It also can be called 4,4'-Diaminodiphenylamine ; 4,4'-Iminodianiline ; AI3-12116 ; Aniline, 4,4'-iminodi- ; Benzenamine, 4,4'-iminobis- ; Bis(p-aminophenyl)amine ; C.I. 76120 ; CI 76120 ; Di(p-aminophenyl)amine ; Diazol Black C ; Indamine ; NSC 33417 ; p,p'-Diaminodiphenylamine ; p-Phenylenediamine, N-(p-aminophenyl)- .

Product Name

4,4'-Iminodianiline

Synthetic route

N-(4-Aminophenyl)-1,4-benzenediamine Chemical Properties

N-(4-Aminophenyl)-1,4-benzenediamine Specification

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