537-65-5

Basic information

• Product Name: 4,4'-Iminodianiline
• Synonyms: 4,4'-Iminodianiline;N-(4-Aminophenyl)-1,4-benzenediamine;Azoic DC 109(base);Blue Black Base NT;C.I.76120;Diazol Black C;1-N-(4-aminophenyl)benzene-1,4-diamine;bis(4-aminophenyl)amine
• CAS NO: 537-65-5
• Molecular Formula: C₁₂H₁₃N₃
• Molecular Weight: 199.25
• EINECS: 208-673-4
• Mol File: 537-65-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 158°C
• Boiling Point: 326.78°C (rough estimate)
• Flash Point: 239.2°C
• Appearance: /
• Density: 1.1470 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 6.15±0.10(Predicted)
• CAS DataBase Reference: 4,4'-Iminodianiline(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Iminodianiline(537-65-5)
• EPA Substance Registry System: 4,4'-Iminodianiline(537-65-5)

Safety Data

• Hazardous Substances Data: 537-65-5(Hazardous Substances Data)

Usage

Chemical Properties

Black brown powder

Purification Methods

Crystallise the amine from pKEst ~water (its solubility at 25o is 0.42%). [Beilstein 13 H 110, 13 I 36, 13 II 55, 13 III 256, 13 IV 203.]

Synthetic route

N-(4-nitrophenyl)-1,4-phenylenediamine (6149-34-4) → 4,4'-diaminodiphenylamine (537-65-5)

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;

N,N-bis(p-nitrophenyl)amine (1821-27-8) → 4,4'-diaminodiphenylamine (537-65-5)

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

Bis-(4-nitro-phenyl)-oxy-aminyl (3313-75-5) → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

N,N-bis-(4-nitro-phenyl)-formamide → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With iron

N-acetyl-4,4'-dinitrodiphenylamine (106038-75-9) → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With iron

aniline hydrochloride (142-04-1) + p-phenylenediamine hydrochloride (540-24-9) → 4,4'-diaminodiphenylamine (537-65-5)

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

aniline hydrochloride (142-04-1) + aniline yellow (60-09-3) + aniline (62-53-3) → 4,4'-diaminodiphenylamine (537-65-5)

p-phenylenediamine hydrochloride (540-24-9) + 1,4-phenylenediamine (106-50-3) → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With water at 200℃;

N-[4-(phenylazo)phenyl]-acetamide (4128-71-6) → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With hydrochloride of tin dichloride

aniline hydrochloride (142-04-1) + aniline (62-53-3) + hydrochloride of p-amino-azobenzene → 4,4'-diaminodiphenylamine (537-65-5)

water (7732-18-5) + 1,4-phenylenediamine (106-50-3) + hydrochloride of/the/ p-phenylenediamine → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
at 200℃;

aniline (62-53-3) + 1,4-phenylenediamine (106-50-3) + potassium dichromate → 4,4'-diaminodiphenylamine (537-65-5)

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

sulfuric acid (7664-93-9) + aniline yellow (60-09-3) + zinc → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
dann mit verd. Schwefelsaeure;

aniline black → 4,4'-diaminodiphenylamine (537-65-5) + 1,4-phenylenediamine (106-50-3)

Conditions	Yield
With hydrogenchloride; tin
With phosphorus; hydrogen iodide

hydrogenchloride (7647-01-0) + N-[4-(phenylazo)phenyl]-acetamide (4128-71-6) + tin dichloride → 4,4'-diaminodiphenylamine (537-65-5) + N-acetyl-4,4'-diaminodiphenylamine (108272-17-9) + aniline (62-53-3) + 1,4-phenylenediamine (106-50-3)

4-amino-azobenzene hydrochloride → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With sulfuric acid; sulfur dioxide; zinc

5-amino-2-<4-amino-anilino>-benzene-sulfonic acid-(1) → 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
With sulfuric acid

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + Bis-(4-nitro-phenyl)-oxy-aminyl (3313-75-5) + tin (II)-chloride → 4,4'-diaminodiphenylamine (537-65-5)

hydrogenchloride (7647-01-0) + N-acetyl-4,4'-diaminodiphenylamine (108272-17-9) → 4,4'-diaminodiphenylamine (537-65-5)

sulfuric acid (7664-93-9) + bis-(4-benzylidenamino-phenyl)-amine (17867-12-8) → 4,4'-diaminodiphenylamine (537-65-5) + benzaldehyde (100-52-7)

diethyl ether (60-29-7) + N,N-bis-(4-nitro-phenyl)-o-trityl-hydroxylamine (861362-54-1) + palladium black → triphenylmethyl alcohol (76-84-6) + 4,4'-diaminodiphenylamine (537-65-5)

Conditions	Yield
Hydrogenation;

diphenylamine (122-39-4) → 4,4'-diaminodiphenylamine (537-65-5)

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

Diphenylaminoxid-Radikal (712-51-6) → 4,4'-diaminodiphenylamine (537-65-5)

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 → 4,4'-diaminodiphenylamine (537-65-5)

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

Nitrosobenzene (586-96-9) → 4,4'-diaminodiphenylamine (537-65-5)

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

1,4-phenylenediamine (106-50-3) + trans-azobenzene (17082-12-1) → 4,4'-diaminodiphenylamine (537-65-5)

4-nitro-aniline (100-01-6) → 4,4'-diaminodiphenylamine (537-65-5)

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

4-Fluoronitrobenzene (350-46-9) → 4,4'-diaminodiphenylamine (537-65-5)

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

1,4-phenylenediamine (106-50-3) → 4,4'-diaminodiphenylamine (537-65-5)

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

4,4'-diaminodiphenylamine (537-65-5) + 2,4-Dinitrofluorobenzene (70-34-8) → N,N'-bis(2'',4''-dinitrophenyl)-4,4'-diaminodiphenylamine

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

4,4'-diaminodiphenylamine (537-65-5) + 4-Fluoronitrobenzene (350-46-9) → N,N’’-bis(4’’-nitrophenyl)-4,4’-diaminodiphenylamine (258269-00-0)

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%

4,4'-diaminodiphenylamine (537-65-5) + ortho-nitrofluorobenzene (1493-27-2) → N,N'-bis(2''-nitrophenyl)-4,4'-diaminodiphenylamine

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 + 4,4'-diaminodiphenylamine (537-65-5) → C70H119N17

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%

4,4'-diaminodiphenylamine (537-65-5) + 4-nitrobenzaldehdye (555-16-8) → 4-[(E)-(4-nitrophenyl)methyleneamino]-N-[4-[(E)-(4-nitrophenyl)methyleneamino]phenyl]aniline (52167-06-3)

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

4,4'-diaminodiphenylamine (537-65-5) + 3-bromo-9-(tertbutyldimethylsilyl)-9H-carbazole → TBSCz5

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%

thiophosgene (463-71-8) + 4,4'-diaminodiphenylamine (537-65-5) → bis(4-isothiocyanatophenyl)amine (1048037-23-5)

Conditions	Yield
In ethanol; water	86%

4,4'-diaminodiphenylamine (537-65-5) + 4-methoxy-benzaldehyde (123-11-5) → 4-[(E)-(4-methoxyphenyl)methyleneamino]-N-[4-[(E)-(4-methoxyphenyl)methylene-amino]phenyl]aniline

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

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + 4,4'-diaminodiphenylamine (537-65-5) → C102H68N8

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;

4,4'-diaminodiphenylamine (537-65-5) + tert-butyl (4'-bromo-[1,1'biphenyl]-4-yl)(phenyl)carbamate → C127H118N8O10

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

4,4'-diaminodiphenylamine (537-65-5) + Cholesteryl chloroformate (7144-08-3) → C68H101N3O4

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

4,4'-diaminodiphenylamine (537-65-5) + N-(4-bromophenyl)-N-phenyl-1-naphthylamine (138310-84-6) → C122H88N8

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 + 4,4'-diaminodiphenylamine (537-65-5) → 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	Yield
With di(tertbutyl)phenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 90℃; for 3h; Inert atmosphere;	80%

4,4'-diaminodiphenylamine (537-65-5) + 4-methyl-benzaldehyde (104-87-0) → 4-[(E)-p-tolylmethyleneamino]-N-[4-[(E)-p-tolylmethyleneamino]phenyl]aniline

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

cycl-isopropylidene malonate (2033-24-1) + 4,4'-diaminodiphenylamine (537-65-5) + trimethyl orthoformate (149-73-5) → C26H25N3O8

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

4,4'-diaminodiphenylamine (537-65-5) + 2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester (173300-83-9) → 4,4'-bis[1,3-di(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine (292634-05-0)

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

4,4'-diaminodiphenylamine (537-65-5) + 4-hydroxy-benzaldehyde (123-08-0) → 4-[(E)-[4-[4-[(E)-(4-hydroxyphenyl)methyleneamino]anilino]phenyl]iminomethyl]phenol

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

4,4'-diaminodiphenylamine (537-65-5) + phenyl Salicylate (118-55-8) → C26H21N3O4

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

4,4'-diaminodiphenylamine (537-65-5) + tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) → 4,4'-bis[2,3-di(tert-butoxycarbonyl)guanidino]diphenylamine

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

4,4'-diaminodiphenylamine (537-65-5) + 4-Fluoronitrobenzene (350-46-9) → N1-(4-aminophenyl)-N4-(4-nitrophenyl)-1,4-benzenediamine

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

Upstream product

• 4128-71-6 N-[4-(phenylazo)phenyl]-acetamide 
• 106-50-3 1,4-phenylenediamine 
• 17082-12-1 trans-azobenzene 
• 98-95-3 nitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 100-01-6 4-nitro-aniline 
• 6149-34-4 N-(4-nitrophenyl)-1,4-phenylenediamine 
• 586-96-9 Nitrosobenzene 
• 712-51-6 Diphenylaminoxid-Radikal 
• 122-39-4 diphenylamine 
• 60-29-7 diethyl ether 
• 861362-54-1 N,N-bis-(4-nitro-phenyl)-o-trityl-hydroxylamine 
• 7664-93-9 sulfuric acid 
• 17867-12-8 bis-(4-benzylidenamino-phenyl)-amine 

Downstream Products

• 140420-00-4 4,4'-(4,4'-Imino-dianilino)-di-phenol 
• 101-78-0 N-(4-Imino-cyclohexa-2,5-dienylidene)-benzene-1,4-diamine 
• 151746-34-8 N,N'-bis(4-aminophenyl)-1,4-benzoquinonediimine 
• 1292320-50-3 2-amino-4-benzyloxy-6-[N-(4-(4-aminophenylamino)anilino)]-5-nitropyrimidine 

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