15721-78-5

Basic information

• Product Name: P,P'-DIOCTYLDIPHENYLAMINE
• Synonyms: AGERITE STALITE S;VANOX 12;VANLUBE-81;VANLUBE(R) 81;P,P'-DIOCTYLDIPHENYLAMINE;bis(4-(1,1,3,3-tetramethylbutyl)phenyl)amine;Benzenamine, 4-(1,1,3,3-tetramethylbutyl)-N-4-(1,1,3,3-tetramethylbutyl)phenyl-;Bis(4-(1,1,3,3-tetramethylbutyl)phenyl)amin
• CAS NO: 15721-78-5
• Molecular Formula: C₂₈H₄₃N
• Molecular Weight: 393.65
• EINECS: 202-965-5
• Product Categories: Organics
• Mol File: 15721-78-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 476.5 °C at 760 mmHg
• Flash Point: 244.9 °C
• Appearance: /
• Density: 0.935 g/cm³
• Vapor Pressure: 3.03E-09mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated
• PKA: 2.00±0.50(Predicted)
• Water Solubility: 52.3-100μg/L at 25-28℃
• CAS DataBase Reference: P,P'-DIOCTYLDIPHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: P,P'-DIOCTYLDIPHENYLAMINE(15721-78-5)
• EPA Substance Registry System: P,P'-DIOCTYLDIPHENYLAMINE(15721-78-5)

Safety Data

• Hazardous Substances Data: 15721-78-5(Hazardous Substances Data)

Usage

Uses

Bis(4-Tert-octylphenyl)amine is a component present in the composition of lubricating grease.

InChI:InChI=1/C28H43N/c1-25(2,3)19-27(7,8)21-11-15-23(16-12-21)29-24-17-13-22(14-18-24)28(9,10)20-26(4,5)6/h11-18,29H,19-20H2,1-10H3

Synthetic route

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 4,4'-di-tert-octyldiphenylnitrosoamine (84077-82-7)

Conditions	Yield
With hydrogenchloride; sodium nitrite In ethanol; isopropyl alcohol at 0 - 5℃; for 1h;	90%

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) + N-(2,6-diisopropylphenyl)-1,6-bis(4-(1,1,3,3-tetramethylbutyl)phenoxy)-9-bromoperylene-3,4-dicarboximide → C90H108N2O4 (937041-84-4)

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 80℃; for 24h; Buchwald Reaction;	88%

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 3,7-di-tert-octyl-phenothiazine (10538-33-7)

Conditions	Yield
With sulfur at 480 - 500℃; Inert atmosphere;	78%
With iodine; sulfur

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) + N-(2,6-diisopropylphen-yl)-9-bromo-perylene-3,4-dicarboximide (165550-62-9) → N-(2,6-diisopropylphenyl)-9-[bis(4-tert-octyl)phenyl]aminoperylene-3,4-dicarboximide (937041-82-2)

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 80℃; for 24h; Buchwald Reaction;	77%

10-chloro-2-(2,6-diisopropylphenyl)-1H-xantheno[2',1',9':10,5,6]anthra[2,1,9-def]isoquinoline-1,3(2H)-dione + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 10-(bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)amino)-2-(2,6-diisopropylphenyl)-1H-xantheno[2',1',9':10,5,6]anthra[2,1,9-def]isoquinoline-1,3(2H)-dione

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; Inert atmosphere;	75%

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) + 1-ethyl 3-alkyl 2-bromo-2-methylpropanedioate → ethyl 3,5-dimethyl-1-(4-methylphenyl)-2-oxoindoline-3-carboxylate

Conditions	Yield
With [2,2]bipyridinyl; copper diacetate; potassium carbonate In acetonitrile at 120℃; for 12h; Schlenk technique; Inert atmosphere;	74%

10-chloro-2-(2,6-diisopropylphenyl)-1H-thioxantheno[2′,1′,9′:10,5,6]anthra[2,1,9-def]isoquinoline-1,3(2H)-dione + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 10-(bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)amino)-2-(2,6-diisopropylphenyl)-1H-thioxantheno[2',1',9':10,5,6]anthra[2,1,9-def]isoquinoline-1,3(2H)-dione

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; Inert atmosphere;	73%

iodobenzene (591-50-4) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline (1197984-29-4)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Buchwald-Hartwig reaction; Inert atmosphere; Reflux;	65%

N-cyclohexyl-4-(4-chloro-2-nitrophenyl)naphthalene-1,8-dicarboximide + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → N-cyclohexyl-4-(4-di(p-tert-octylphenyl)amino-2-nitrophenyl)naphthalene-1,8-dicarboximide

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 16h; Inert atmosphere;	64%

2-bromothiophene (1003-09-4) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 2-(N,N-bis(4-tert-octylphenyl)amino)thiophene (1492797-77-9)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 16h; Reflux;	62%

N-(2,6-diisopropylphenyl)-1,6,9,14-tetra[4-(1,1,3,3-tetramethyl-butyl)phenoxy]-11-bromo-terrylene-3,4-dicarboxylic acid imide (914387-26-1) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → N-(2,6-diisopropylphenyl)-1,6,9,14-tetra[(4-tert-octyl)phenoxy]-9-[bis(4-tert-octyl)phenyl]aminoterrylene-3,4-dicarboximide (937041-94-6)

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 80℃; for 16h; Buchwald Reaction;	61%

1.4-dibromobenzene (106-37-6) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 4-bromo-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline (937041-96-8)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 7h; Inert atmosphere;	60%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; for 72h;	36%

4-Fluoronitrobenzene (350-46-9) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 4-nitro-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline (937041-72-0)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere;	60%

ethyl 2-bromoisobutyrate (600-00-0) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 3,3-dimethyl-5-(2,4,4-trimethylpentan-2-yl)-1-(4-(2,4,4-trimethylpentan-2-yl)phe nyl)indolin-2-one

Conditions	Yield
With [2,2]bipyridinyl; copper diacetate; potassium carbonate In acetonitrile at 120℃; for 12h; Schlenk technique; Inert atmosphere;	59%

para-nitrophenyl bromide (586-78-7) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 4-nitro-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline (937041-72-0)

Conditions	Yield
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) at 20 - 90℃; for 16h;	45%

9,10-dibromo-1,6,7,12-tetrachloro-3,4-perylenedicarboxylic acid anhydride (1402905-24-1) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 5,6,14,15-tetrachloro-11-(2,4,4-trimethylpentan-2-yl)-8-(4-(2,4,4-trimethylpentan-2-yl)phenyl)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-mna]acridine-1,3(8H)-dione

Conditions	Yield
Stage #1: 9,10-dibromo-1,6,7,12-tetrachloro-3,4-perylenedicarboxylic acid anhydride; di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine With palladium diacetate; sodium t-butanolate; tricyclohexylphosphine In toluene at 100℃; for 24h; Inert atmosphere; Stage #2: With acetic acid In dichloromethane at 70℃;	38%

4-[bis-(4-iodophenyl)amino]benzaldehyde (808758-81-8) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 4-(bis(4-(bis(4-(1,1,3,3-tetramethylbutyl)phenyl)amino)phenyl)amino)benzaldehyde

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 48h; Reflux; Inert atmosphere;	34%

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) + methyl iodide (74-88-4) → N-methyl-4-(2,4,4-trimethylpentan-2-yl)-N-(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline

Conditions	Yield
Stage #1: di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine With sodium hydride In tetrahydrofuran for 1.5h; Stage #2: methyl iodide In tetrahydrofuran for 16h;	32%

6,7-dibromo-1H,3H-naphtho<1,8-cd>pyran-1,3-dione (13577-26-9) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 9-(2,4,4-trimethylpentan-2-yl)-6-(4-(2,4,4-trimethylpentan-2-yl)phenyl)-1H-isochromeno[6,5,4-mna]acridine-1,3(6H)-dione

Conditions	Yield
Stage #1: 6,7-dibromo-1H,3H-naphtho<1,8-cd>pyran-1,3-dione; di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; Inert atmosphere; Stage #2: With acetic anhydride; acetic acid In dichloromethane at 20℃;	25%

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) + 5,8,12-tribromo-2-(2,6-diisopropylphenyl)-1H-benzo[5,10]anthra[2,1,9-def]isoquinoline-1,3(2H)-dione (165550-65-2) → C118H150N4O2 (937042-32-5)

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 80℃; for 48h; Buchwald Reaction;	10%

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → Di-(4-dimethylneopentylmethylphenyl)nitroxid-Radikal

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether; oxygen In dimethyl sulfoxide at 25℃; Product distribution; base-catalysed oxidation of secondary amines, possible mechanism, paramagnetic and diamagnetic oxidation products, ESR and GC-MS study;

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 1,1-di-(4-tert-octylphenyl)hydrazine

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / sodium nitrite, aq. HCl / propan-2-ol; ethanol / 1 h / 0 - 5 °C 2: Zn, AcOH / propan-2-ol / 3.5 h / 20 - 25 °C View Scheme

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 2,2-di-(4-tert-octylphenyl)picrylhydrazine (84077-83-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / sodium nitrite, aq. HCl / propan-2-ol; ethanol / 1 h / 0 - 5 °C 2: Zn, AcOH / propan-2-ol / 3.5 h / 20 - 25 °C 3: sodium bicarbonate / propan-2-ol / 0.5 h / Heating View Scheme

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl, free radical (84077-81-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / sodium nitrite, aq. HCl / propan-2-ol; ethanol / 1 h / 0 - 5 °C 2: Zn, AcOH / propan-2-ol / 3.5 h / 20 - 25 °C 3: sodium bicarbonate / propan-2-ol / 0.5 h / Heating 4: 74 percent / PbO2, Na2SO4 / CHCl3 / 1 h / 25 °C View Scheme

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 3,7-bis-(1,1,3,3-tetramethyl-butyl)-phenothiazine-5,5-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine; sulfur 2: aqueous H2O2; acetic acid View Scheme

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → N,N-bis(4-bromophenyl)-N',N'-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)-1,4-phenylenediamine (1213714-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / dimethyl sulfoxide / 48 h / 120 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrazine hydrate / ethanol / Inert atmosphere; Reflux 3: 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate / toluene / 6 h / Inert atmosphere; Reflux View Scheme

di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → 5-(N,N-bis(4-tert-octylphenyl)amino)-2-(tri-n-butylstannyl)thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate / toluene / 16 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C 2.2: 16.5 h / -78 - 20 °C View Scheme

N-(1'-ethylpropyl)-8-bromo-10-(bis(4-(2,4,4-trimethylpentane-2-yl)phenyl)amino)perylene-3,4-dicarboximide (1554688-71-9) + di[p-(2,4,4-trimethyl-2-pentyl)phenyl]amine (15721-78-5) → N-(1'-ethylpropyl)-9,11-bis(bis(4-(2,4,4-trimethylpentane-2-yl)phenyl)amino)perylene-3,4-dicarboximide (1554688-59-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; Inert atmosphere;	40 mg
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; Inert atmosphere;	40 mg

Downstream Products

• 10538-33-7 3,7-di-tert-octyl-phenothiazine 
• 1197984-29-4 N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline 
• 937041-72-0 4-nitro-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline 
• 1213714-81-8 N,N-bis(4-bromophenyl)-N',N'-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)-1,4-phenylenediamine 
• 1492797-77-9 2-(N,N-bis(4-tert-octylphenyl)amino)thiophene 
• 937042-32-5 C₁₁₈H₁₅₀N₄O₂ 
• 937041-94-6 N-(2,6-diisopropylphenyl)-1,6,9,14-tetra[(4-tert-octyl)phenoxy]-9-[bis(4-tert-octyl)phenyl]aminoterrylene-3,4-dicarboximide 
• 937041-84-4 C₉₀H₁₀₈N₂O₄ 
• 937041-82-2 N-(2,6-diisopropylphenyl)-9-[bis(4-tert-octyl)phenyl]aminoperylene-3,4-dicarboximide 

Relevant articles and documents

Process for the isolation of alkylated aromatic amines

Alkylated aromatic amines can be isolated from crude catalyst-containing mixtures of these with olefins by a procedure in which in general equivalent amounts of an inorganic base and water are added to the alkylation mixture, the catalyst is hydrolysed, the water present in the reaction mixture after the hydrolysis is removed by distillation and the solid catalyst residue is separated off. The catalyst-free alkylation mixture which remains is then fed to customary further working up.