2350-01-8

Basic information

• Product Name: N,N-Diphenyl-p-phenylenediamine
• Synonyms: N,N'-DIPHENYL-P-PHENYLENEDIAMINE;(4-aminophenyl)-di(phenyl)amine;1-N,1-N-di(phenyl)benzene-1,4-diamine;N1,N1-di(phenyl)benzene-1,4-diamine;N1,N1-diphenyl-1,4-benzenediamine
• CAS NO: 2350-01-8
• Molecular Formula: C₁₈H₁₆N₂
• Molecular Weight: 260.33
• EINECS: 200-806-4
• Mol File: 2350-01-8.mol
• Article Data: 40

Chemical Properties

• Melting Point: 144.0 to 148.0 °C
• Boiling Point: 270°C/57mmHg(lit.)
• Flash Point: 193.3 °C
• Appearance: /
• Density: 1.168 g/cm³
• Vapor Pressure: 7.78E-08mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.20±0.10(Predicted)
• CAS DataBase Reference: N,N-Diphenyl-p-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diphenyl-p-phenylenediamine(2350-01-8)
• EPA Substance Registry System: N,N-Diphenyl-p-phenylenediamine(2350-01-8)

Safety Data

• Hazardous Substances Data: 2350-01-8(Hazardous Substances Data)

Usage

General Description

N,N-Diphenyl-p-phenylenediamine, commonly known as DPPD, is a chemical compound used primarily as an antioxidant in rubber and in petroleum products. It is a solid, white to light pink crystalline substance that is insoluble in water but soluble in organic solvents. DPPD is added to rubber and petroleum products to prevent oxidation and deterioration, thereby extending their shelf life and usage. It is also used as a stabilizer in plastics and polymers, as well as an intermediate in the production of various dyes and pigments. However, DPPD has been associated with skin irritation and sensitization, and its use is regulated in some countries due to potential health and environmental concerns.

InChI:InChI=1/C18H16N2/c19-15-11-13-18(14-12-15)20(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14H,19H2

Synthetic route

4-nitrophenyldiphenylamine (4316-57-8) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With tin; acetic acid	98%
With tin; acetic acid	98%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 3000.3 Torr; for 3h;	96%

4-bromo-N-(4-bromophenyl)-N-(4-nitrophenyl)amine (144393-34-0) → 1-N,1-N-bis(4-bromophenyl)benzene-1,4-diamine + 4-amino-3,4',4''-tribromotriphenylamine + 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Stage #1: 4-nitrophenyl-bis(4'-bromophenyl)amine With tin; acetic acid at 75℃; for 1h; Stage #2: at 65℃; for 9h;	A 87% B 12% C 1%

4-N,N-diphenylamino-1-bromobenzene (36809-26-4) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With tri-tert-butyl phosphine; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 20h;	77%
Stage #1: 4-N,N-diphenylamino-1-bromobenzene With tri-tert-butyl phosphine; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 4h; Inert atmosphere; Stage #2: With trifluoroacetic acid	74%
With copper(l) iodide; ammonia; caesium carbonate In water; N,N-dimethyl-formamide; acetylacetone at 100℃; for 12h;
Multi-step reaction with 2 steps 1: sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 20 h / 95 °C / Inert atmosphere 2: hydrogenchloride / tetrahydrofuran; water / 0.5 h / 20 °C View Scheme

(p-chlorophenyl)diphenylamine (4316-56-7) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 65℃; for 24h; Inert atmosphere; chemoselective reaction;	68%

diphenylamine (122-39-4) + 4-bromo-aniline (106-40-1) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With water; sodium t-butanolate In N,N-dimethyl-formamide at 120℃; for 10h; Schlenk technique;	55%

N,N,N'-triphenylhydrazine (606-88-2) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

hydrogenchloride (7647-01-0) + 4-nitrophenyldiphenylamine (4316-57-8) + tin → 4-aminotriphenylamine (2350-01-8)

ethanol (64-17-5) + 4-nitrophenyldiphenylamine (4316-57-8) + acetic acid (64-19-7) + zinc → 4-aminotriphenylamine (2350-01-8)

4-bromo-N-(4-bromophenyl)-N-(4-nitrophenyl)amine (144393-34-0) → 4-amino-4'-bromotriphenylamine + 4-amino-3,4'-dibromotriphenylamine + 4-amino-3,4',4''-tribromotriphenylamine + 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With tin; acetic acid for 8h; Heating; Further byproducts given;	A 6 % Chromat. B 13 % Chromat. C 32 % Chromat. D 4 % Chromat.

diphenylamine (122-39-4) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / dimethylformamide 2: hydrazine / Pd/C / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / dimethylsulfoxide / 10 h / 145 - 150 °C 2: Sn; aq. HCl / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3; copper; nitrobenzene 2: zinc; alcohol; glacial acetic acid / unter Kuehlung View Scheme

4-Fluoronitrobenzene (350-46-9) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / dimethylformamide 2: hydrazine / Pd/C / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / dimethylsulfoxide / 10 h / 145 - 150 °C 2: Sn; aq. HCl / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl acetamide / 0.5 h / 20 °C 1.2: 1 h / 100 °C 2.1: palladium on activated charcoal; hydrazine hydrate / ethanol / 12 h / Reflux View Scheme

N,N-diphenylaminobenzene (603-34-9) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 41 percent / copper(II) nitrate; acetyc anhydride / 2 h / 20 °C 2: 98 percent / tin; acetic acid View Scheme
Multi-step reaction with 3 steps 1: 41 percent / acetic anhydride; copper(II) nitrate / 2 h / 20 °C 2: 99 percent / Br2 / CH2Cl2 / 36 h 3: 4 percent Chromat. / tin; AcOH / 8 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: 41 percent / acetic anhydride; copper(II) nitrate / 2 h / 20 °C 2.1: 99 percent / Br2 / CH2Cl2 / 36 h 3.1: tin; AcOH / 1 h / 75 °C 3.2: 1 percent / 9 h / 65 °C View Scheme

benzene diazonium chloride (100-34-5) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium ferrocyanide / Behandlung mit Zinkstaub und Ammoniak 2: concentrated hydrochloric acid; tin dichloride View Scheme

p-nitrobenzene iodide (636-98-6) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3; copper; nitrobenzene 2: zinc; alcohol; glacial acetic acid / unter Kuehlung View Scheme

aniline (62-53-3) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate; water / N,N-dimethyl-formamide / 3 h / 120 °C / Schlenk technique 2: sodium t-butanolate; water / N,N-dimethyl-formamide / 10 h / 120 °C / Schlenk technique View Scheme
Multi-step reaction with 2 steps 1: sodium t-butanolate; tetrabutylammomium bromide / toluene / 7 h / 105 °C / Schlenk technique 2: sodium t-butanolate; water / N,N-dimethyl-formamide / 10 h / 120 °C / Schlenk technique View Scheme

N1-(diphenylmethylene)-N4,N4-diphenyl-1,4-benzenediamine → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.5h;
With hydrogenchloride In tetrahydrofuran; water at 22℃; Inert atmosphere; Schlenk technique;	0.193 g

diphenylamine (122-39-4) + 4-Fluoronitrobenzene (350-46-9) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Stage #1: diphenylamine; 4-Fluoronitrobenzene With sodium hydride Stage #2: With palladium on activated charcoal; hydrazine

bromochlorobenzene (106-39-8) + diphenylamine (122-39-4) → 4-aminotriphenylamine (2350-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate; ruphos; allyl(2-di-tert-butylphosphino-2‘,4‘,6‘-triisopropyl-1,1‘-biphenyl)palladium(II) triflate / tetrahydrofuran / 22 - 80 °C / Sealed tube; Inert atmosphere; Schlenk technique 2: hydrogenchloride / tetrahydrofuran; water / 22 °C / Inert atmosphere; Schlenk technique View Scheme

2,5-thiophenedicarboxaldehyde (932-95-6) + 4-aminotriphenylamine (2350-01-8) → C42H32N4S

Conditions	Yield
With toluene-4-sulfonic acid In chloroform; isopropyl alcohol for 72h; Solvent; Inert atmosphere; Reflux;	98%
With toluene-4-sulfonic acid In chloroform at 60℃; Inert atmosphere;	80%

4-aminotriphenylamine (2350-01-8) + acryloyl chloride (814-68-6) → N-(4-(diphenylamino)phenyl)acrylamide (176652-15-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 24h; Cooling with ice;	92%
Stage #1: 4-aminotriphenylamine; acryloyl chloride With sodium carbonate In tetrahydrofuran at -5 - 0℃; for 2h; Stage #2: With sodium carbonate In tetrahydrofuran; water	82%

4-aminotriphenylamine (2350-01-8) + 4-bromo-benzaldehyde (1122-91-4) + 9,10-phenanthrenequinone (84-11-7) → C39H26BrN3

Conditions	Yield
With ammonium acetate; acetic acid at 120℃; Inert atmosphere;	92%
With ammonium acetate In acetic acid at 115℃; for 12h; Inert atmosphere;	85%
With ammonium acetate; acetic acid at 120℃; for 2h; Inert atmosphere;

phthalic anhydride (85-44-9) + 4-aminotriphenylamine (2350-01-8) → N-(4-diphenylaminophenyl)phthalimide

Conditions	Yield
Stage #1: phthalic anhydride; 4-aminotriphenylamine With N,N-dimethyl acetamide at 20℃; for 2h; Stage #2: With pyridine; acetic anhydride at 110℃; for 3h;	90%

1,8-Naphthalic anhydride (81-84-5) + 4-aminotriphenylamine (2350-01-8) → N-(4-diphenylaminophenyl)-1,8-naphthalimide

Conditions	Yield
With isoquinoline; 3-methyl-phenol at 180℃; for 18h;	90%

4-aminotriphenylamine (2350-01-8) + 4-(4-bromophenyl)bromobenzene (92-86-4) → N,N'-bis(p-(diphenylamino)phenyl)benzidine (1353442-60-0)

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 70℃; for 20h;	90%

5,5'-(2,1,3-benzothiadiazole-4,7-diyl)bis-(2-thiophenecarboxaldehyde) (882303-63-1) + 4-aminotriphenylamine (2350-01-8) → C52H36N6S3

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 60℃; Inert atmosphere;	88%
With toluene-4-sulfonic acid In chloroform at 60℃; Inert atmosphere;	80%

2,2'-bithiophene-5-carboxaldehyde (3779-27-9) + 4-aminotriphenylamine (2350-01-8) → C27H20N2S2

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	86%

4-aminotriphenylamine (2350-01-8) + salicylaldehyde (90-02-8) → 2-(((4-(diphenylamino)phenyl)imino)methyl)phenol (1415476-89-9)

Conditions	Yield
In ethanol for 4h; Reflux; Inert atmosphere; Schlenk technique;	85%
In ethanol for 2h; Inert atmosphere; Reflux;

4-aminotriphenylamine (2350-01-8) + Pyromellitic dianhydride (89-32-7) → N,N’-bis(4-diphenylaminophenyl)pyromellitimide

Conditions	Yield
Stage #1: 4-aminotriphenylamine; Pyromellitic dianhydride With N,N-dimethyl acetamide at 20℃; for 2h; Stage #2: With pyridine; acetic anhydride at 110℃; for 3h;	85%

4-aminotriphenylamine (2350-01-8) + meso-mesityl-α,α’-dichlorodipyrrin → 9-(4-diphenylaminophenyl)amino-1-chloro-5-mesityldipyrrin

Conditions	Yield
In acetonitrile at 20℃; for 17h; Inert atmosphere;	83%

4-aminotriphenylamine (2350-01-8) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1-(((4-(diphenylamino)phenyl)imino)methyl)naphthalen-2-ol (1415476-90-2)

Conditions	Yield
In ethanol for 4h; Reflux; Inert atmosphere; Schlenk technique;	82%

4-aminotriphenylamine (2350-01-8) + 4-cyanobenzaldehyde (105-07-7) + benzil (134-81-6) → 4-(1-(4-(diphenylamino)phenyl)-4,5-diphenyl-1H-imidazole-2-yl)benzonitrile

Conditions	Yield
With ammonium acetate In acetic acid Inert atmosphere; Reflux;	78%

4-aminotriphenylamine (2350-01-8) + 3-bromo-9-(4-vinylphenyl)-9H-carbazole → C38H29N3

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 8h;	77.8%

2-bromonaphthalene (580-13-2) + 4-aminotriphenylamine (2350-01-8) → N1-(naphthalen-2-yl)-N4,N4-diphenylbenzene-1,4-diamine

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In tetrahydrofuran at 100℃; for 3h; Inert atmosphere;	75%

thiophene-2-carbaldehyde (98-03-3) + 4-aminotriphenylamine (2350-01-8) → C23H18N2S

Conditions	Yield
With acetic acid In tetrahydrofuran at 60℃; for 4h; Inert atmosphere;	73.1%

4-aminotriphenylamine (2350-01-8) + 2-bromo-9,9-dimethyl-9H-fluorene (28320-31-2) → C33H28N2 (885684-28-6)

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 20℃; for 5h;	71%
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃; for 12h;

ferrocenecarboxaldehyde (12093-10-6) + 4-aminotriphenylamine (2350-01-8) → (E)-N-(4-(diphenylamino)phenyl)formimidoyl ferrocene

Conditions	Yield
With aluminum oxide In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 10h; Inert atmosphere;	70.28%

4-aminotriphenylamine (2350-01-8) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → N,N’-bis(4-diphenylaminophenyl)naphthalene-1,4,5,8-tetracarboxylic diimide

Conditions	Yield
With isoquinoline; 3-methyl-phenol at 180℃; for 18h;	70%

4-aminotriphenylamine (2350-01-8) + chloroacetyl chloride (79-04-9) → C20H17ClN2O

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	68.22%

4-aminotriphenylamine (2350-01-8) + C96H78Cl2N4O8 → C114H92N6O8

Conditions	Yield
With potassium tert-butylate; palladium diacetate; tricyclohexylphosphine In toluene at 110℃; for 7h; Buchwald-Hartwig Coupling;	67.2%

4-bromo-N-((4-bromophenyl)chloromethylene)benzhydrazonoyl chloride (837429-72-8) + 4-aminotriphenylamine (2350-01-8) → 3,5-bis-(4-bromophenyl)-4-([4-(N,N-di(phenyl)amino)]phen-1-yl)-1,2,4-triazole (1151695-71-4)

Conditions	Yield
With N,N-dimethyl-aniline at 135℃; for 12h; Inert atmosphere;	67%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 72h;	65%

4-aminotriphenylamine (2350-01-8) + 4,5,7-trinitro-9-oxofluorene-2-carbonyl chloride (53410-48-3) → 4,5,7-Trinitro-9-oxo-9H-fluorene-2-carboxylic acid (4-diphenylamino-phenyl)-amide

Conditions	Yield
In acetone Heating;	65%

4-aminotriphenylamine (2350-01-8) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N’-bis(4-diphenylaminophenyl)perylene-3,4,9,10-tetracarboxylic diimide

Conditions	Yield
With isoquinoline; 3-methyl-phenol at 180℃; for 18h;	65%

4-aminotriphenylamine (2350-01-8) + 2Cl-diPBI (1172630-55-5) → C114H90N6O8 (1247944-78-0)

Conditions	Yield
With potassium tert-butylate; palladium diacetate; tricyclohexylphosphine In toluene at 110℃; for 5h; Buchwald-Hartwig Reaction; Inert atmosphere;	63.4%

Upstream product

• 7647-01-0 hydrogenchloride 
• 4316-57-8 4-nitrophenyldiphenylamine 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 122-39-4 diphenylamine 
• 106-40-1 4-bromo-aniline 
• 62-53-3 aniline 
• 106-39-8 bromochlorobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 36809-26-4 4-N,N-diphenylamino-1-bromobenzene 
• 4316-56-7 (p-chlorophenyl)diphenylamine 
• 636-98-6 p-nitrobenzene iodide 
• 100-34-5 benzene diazonium chloride 
• 144393-34-0 4-bromo-N-(4-bromophenyl)-N-(4-nitrophenyl)amine 

Downstream Products

• 19742-67-7 4-(diphenylamino)phenyl isocyanate 
• 844658-08-8 N,N-bis(4-nitrophenyl)-N',N'-diphenyl-1,4-phenylenediamine 
• 885684-39-9 C₃₆H₃₂N₂ 
• 1356174-83-8 C₅₁H₃₈N₂S 
• 1151695-71-4 3,5-bis-(4-bromophenyl)-4-([4-(N,N-di(phenyl)amino)]phen-1-yl)-1,2,4-triazole 
• 1091602-96-8 C₃₂H₂₂F₂N₄ 
• 29344-76-1 N₁-(4-(diphenylamino)phenyl)-N₄,N₄-diphenylbenzene-1,4-diamine 

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