Diphenylamine supplier | CasNO.122-39-4

Name
Diphenylamine
EINECS 204-539-4
CAS No. 122-39-4
Article Data910
CAS DataBase
Density 1.088 g/cm³
Solubility 0.03 g/100 mL in water
Melting Point 52 °C
Formula C₁₂H₁₁N
Boiling Point 302 °C at 760 mmHg
Molecular Weight 169.226
Flash Point 152.8 °C
Transport Information UN 3077 9/PG 3
Appearance white crystals or powder
Safety 28-36/37-45-60-61-28A-16-7
Risk Codes 23/24/25-33-50/53-52/53-39/23/24/25-11
Molecular Structure
Hazard Symbols T,N,F
Synonyms Anilinobenzene;Benzene, (phenylamino)-;DFA;DPA;N,N-Diphenylamine;N-Phenylaniline;N-Phenylbenzenamine;NSC 215210;Naugalube 428L;No-Scald;Benzenamine,N-phenyl-;
PSA 12.03000
LogP 3.50320

Synthetic route

: 108-86-1
bromobenzene

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; Pd{dba(OMe)}2 In toluene at 25℃; for 0.166667h; Buchwald-Hartwig cross coupling reaction;	100%
With potassium ethoxide In 1,4-dioxane at 200℃; Catalytic behavior; Buchwald-Hartwig Coupling;	100%
With C31H26N4PPdS(1+)*Cl(1-); sodium t-butanolate In toluene at 95℃; for 14h; Catalytic behavior;	100%

: 1132-38-3
N-cyclohexylidenebenzenamine

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
palladium-carbon In diethylene glycol dimethyl ether; water; nitrobenzene; benzene	100%
palladium-carbon In water; nitrobenzene; benzene	100%
palladium-carbon In diethylene glycol dimethyl ether; water; nitrobenzene; benzene	100%

: 607-00-1
diphenylformamide

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; water for 0.166667h; Ambient temperature;	100%
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 110℃; under 15001.5 Torr; for 3h; Catalytic behavior;	99%
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 100℃; under 37503.8 Torr; for 24h; Autoclave; Glovebox;	86%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amide](carbonyl)(hydride)iron(II); hydrogen In tetrahydrofuran at 100℃; under 22801.5 Torr; for 4h; Catalytic behavior;

: 591-50-4
iodobenzene

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
[1,3-{bis-N-(N-methylimidazolylidene)methyl}-5-methylbenzenecopper dibromide]; caesium carbonate at 170℃; for 12h; Conversion of starting material;	100%
[(N,N-dipyridyl-imidazolylidene)copper dibromide]; caesium carbonate at 170℃; for 12h; Conversion of starting material;	100%
With C31H26N4PPdS(1+)*Cl(1-); sodium t-butanolate In toluene at 95℃; for 10h; Catalytic behavior;	100%

: 62-53-3
aniline

: 98-80-6
phenylboronic acid

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; fac-tris(2-phenylpyridinato-N,C2')iridium(III); copper diacetate; n-tetradecanoic acid In toluene; acetonitrile at 35℃; for 20h; Chan-Lam Coupling; Irradiation;	100%
With copper diacetate; potassium carbonate; benzoic acid In ethyl acetate at 80℃; for 4h; air;	98%
With potassium carbonate In water at 20℃; Reagent/catalyst; Solvent;	95%

: diphenyl-carbamic acid allyl ester

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 1h;	100%

1N-NaOH: 1N-NaOH

: 1132-38-3
N-cyclohexylidenebenzenamine

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
palladium-carbon In diethylene glycol dimethyl ether; water; nitrobenzene; benzene	100%
palladium-carbon In diethylene glycol dimethyl ether; water; nitrobenzene; benzene	100%
palladium-carbon In water; nitrobenzene; benzene	99.4%
palladium-carbon In water; nitrobenzene; benzene	99.4%

: 1321455-60-0
1-tert-butyl-1,1-dimethyl-N,N-diphenylsilanamine

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With silica gel In ethanol; water at 20℃; for 2h;	100%

: 62-53-3
aniline

: 100-58-3
phenylmagnesium bromide

A: 92-52-4
biphenyl

B: 122-39-4
diphenylamine

Conditions

Conditions	Yield
Stage #1: aniline With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: phenylmagnesium bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique;	A n/a B 100%

Yield

Stage #1: aniline With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: phenylmagnesium bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique;

A n/a
B 100%

...Expand

: 62-53-3
aniline

: 108-90-7
chlorobenzene

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; Ni(PPh3)2(1-(p-acetylnaphthyl))Cl In 1,4-dioxane at 100℃;	99%
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere;	99%
With sodium t-butanolate In toluene at 110℃; Inert atmosphere; Glovebox; chemoselective reaction;	99%

: 28719-46-2
triphenylbismuth bis(trifluoroacetate)

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
copper In dichloromethane for 0.5h; Ambient temperature;	99%

: 640-60-8
toluene-4-sulfonic acid phenyl ester

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With (1,3-bis(2,6-diisopropylphenyl)imidazolidene)Ni(styrene)2; lithium tert-butoxide In 1,4-dioxane for 10h; Inert atmosphere; Heating; Schlenk technique;	99%
With potassium hydroxide; [(N,N-dimethylbenzylamine)(trifluoroacetato)palladium(II)]2; XPhos In water at 80℃; for 16h;	91%
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; potassium phosphate; palladium diacetate; phenylboronic acid In butan-1-ol at 110℃; for 2h; Inert atmosphere;	99 %Chromat.

: 4051-56-3
N,N-diphenylbenzamide

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 130℃; under 37503.8 Torr; for 3h; Catalytic behavior;	99%
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	78%
Stage #1: N,N-diphenylbenzamide With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	73%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

: 92-84-2
10H-phenothiazine

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With 3-Hydroxy-1-methylpiperidine; nickel diacetate; sodium hydride In tetrahydrofuran at 65℃; for 4h;	98%
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol for 1h; Mechanism; Ambient temperature; kinetic isotope effect; desulfurization of other benzo- and dibenzothiophenes;	68%
bei der Zinkstaub-Destillation;

: 4-[(diphenylamino)-methyl]-benzonitrile

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With Triethylgermyl-natrium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 68h;	98%

: 17763-67-6
Phenyl triflate

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With C46H27F24FeNiP2(1+)*CF3O3S(1-); triethylamine In 2-methyltetrahydrofuran at 100℃; for 16h; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;	98%
With [(2,6-bis(2,4,6-triisopropylphenyl)phenyl)dicyclohexylphosphine](allyl-η3)palladium(II) chloride; potassium hydrogencarbonate In dodecane; tert-butyl alcohol at 100℃; for 12h; Inert atmosphere; Sealed tube;	92%
With caesium carbonate; palladium diacetate In toluene at 100℃; for 10h;
With palladium diacetate; caesium carbonate; XPhos In toluene at 100℃; for 1.5h;
With XPhos; palladium diacetate; caesium carbonate In toluene at 20 - 100℃; Inert atmosphere;

: 108-86-1
bromobenzene

Ph5FcP(t-BU)2: Ph5FcP(t-BU)2

Pd(dba)2/Ph5FcP(t-Bu)2: Pd(dba)2/Ph5FcP(t-Bu)2

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With aniline; sodium t-butanolate; Pd(dba)2 In chlorobenzene; toluene	98%

...Expand

: 108-95-2
phenol

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With palladium on activated carbon; ammonium formate; lithium hydroxide In m-xylene at 160℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;	98%
Multi-step reaction with 2 steps 1: Inert atmosphere 2: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere View Scheme
With ammonium formate In 1,3,5-trimethyl-benzene at 140℃; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	73 %Chromat.

: 591-50-4
iodobenzene

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With L-arginine; potassium hydroxide In water at 80℃; under 760.051 Torr; for 2h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	98%
With potassium phosphate; copper(l) iodide; lithium amide In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; chemoselective reaction;	90%
Multi-step reaction with 2 steps 1: ammonia / water / 16 h / 75 °C / Ionic liquid 2: Cu2O nanoparticles (Cu2O-NPs) synthesized in n-Bu4POAc from CuCO3 / 16 h / 75 °C / Ionic liquid View Scheme

: 102078-86-4
N-carbobenzyloxydiphenylamine

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation;	98%

: 16156-59-5
phenyl methanesulfonate

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine In 1,4-dioxane; tert-butyl alcohol at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; chemoselective reaction;	98%

: 66950-63-8
phenyl N,N-dimethylsulfamate

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With sodium t-butanolate In ethylene glycol at 100℃; for 12h;	97%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate In toluene at 20 - 105℃; Inert atmosphere;	94%
With bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;	77%
With sodium t-butanolate; bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;	77%
With (1,2-dimethoxyethane)dichloronickel(II); 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 23 - 80℃; for 4h; Inert atmosphere;	63%

: 639-58-7
triphenyltin chloride

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With triethylamine at 95℃; Catalytic behavior; Reagent/catalyst; Temperature;	97%
With triethylamine at 90℃; for 12h; Reagent/catalyst; Temperature; Stille Cross Coupling;	96%
With triethylamine at 20℃; for 15h; Catalytic behavior; Temperature;	95%
With copper diacetate; triethylamine at 20℃; for 24h;	94%

: 519-87-9
N,N-diphenylacetamide

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 110℃; under 22502.3 Torr; for 3h; Catalytic behavior;	96%
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	89%
Stage #1: N,N-diphenylacetamide With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	83%

: 28899-97-0
triphenylbismuth(V) diacetate

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
copper In dichloromethane for 2h; Ambient temperature;	96%
With copper(II) dipivaloate In dichloromethane for 0.0833333h; Ambient temperature;	100 % Chromat.

: 370839-63-7
N,N-diphenylpyridine-2-sulfonamide

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With magnesium In methanol at 0℃; for 1h;	96%

: 591-50-4
iodobenzene

: 62-53-3
aniline

A: 603-34-9
N,N-diphenylaminobenzene

B: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With [2,2]bipyridinyl; potassium tert-butylate; copper(l) iodide In toluene at 115℃; for 3.5h; Product distribution; Further Variations:; Reagents;	A 95% B 2%
With copper at 180℃; for 12h;	A 46% B 31%
With copper(l) iodide; cesium fluoride In dimethyl sulfoxide at 130℃; for 24h; Ullmann Condensation; Inert atmosphere; Glovebox;	A 12% B 39 %Chromat.
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 110℃; for 3.5h; Product distribution; Further Variations:; Catalysts; high pressure;

...Expand

: 519-87-9
N,N-diphenylacetamide

A: 64-17-5
ethanol

B: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With hydrogen In toluene at 160℃; under 45004.5 Torr; for 15h; Catalytic behavior; Autoclave;	A 89 %Chromat. B 95%
With cis-[Ru(CH3CN)2(η3-C3H5)(CO1,5-cyclooctadiene)]BF4; hydrogen; potassium hexamethylsilazane; (2-aminoethyl)diphenylphosphane In tetrahydrofuran at 100℃; under 38002.6 Torr; for 24h; Autoclave;
With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 18h; Autoclave;	A 96 %Chromat. B 96 %Chromat.
With C16H25MnN3O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In cyclohexane at 100℃; under 22502.3 Torr; for 16h; Inert atmosphere; Autoclave;	A 80 %Chromat. B 82 %Chromat.

: 1369416-85-2
N,N-diphenyloctanamide

A: 111-87-5
octanol

B: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With hydrogen; sodium methylate; [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II) In methanol at 100℃; under 37503.8 Torr; for 16h; Autoclave;	A 77% B 95%

: 506-68-3
bromocyane

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
With trimethylamine Ambient temperature;	100%
With magnesium carbonate In water; acetonitrile for 288h; Heating;	54%

: 122-39-4
diphenylamine

: 79-04-9
chloroacetyl chloride

: 5428-43-3
2-chloro-N,N-diphenylacetamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.333333h;	100%
In toluene at 90℃; for 4h; Inert atmosphere;	99%
In N,N-dimethyl-formamide at 80℃; for 2h;	97%

: 122-39-4
diphenylamine

: 16292-17-4
bis(4-bromophenyl)amine

Conditions

Conditions	Yield
With N-Bromosuccinimide Bromination;	100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 6h; Inert atmosphere;	100%
With tetra-N-butylammonium tribromide In chloroform for 0.0333333h; Ambient temperature;	99%

: 122-39-4
diphenylamine

: 382165-80-2
N-nitrosodiphenylamine

Conditions

Conditions	Yield
With oxalic acid; sodium nitrite In dichloromethane for 5h; Ambient temperature;	100%
With [NO(1+)18-crown-6H(NO3)2(1-)] In dichloromethane at 20℃; for 0.0833333h;	100%
With sodium azide In water; acetonitrile at 20℃;	100%

: 75-15-0
carbon disulfide

: 122-39-4
diphenylamine

: 112492-65-6
lithium N,N-diphenyl dithiocarbamate

Conditions

Conditions	Yield
With lithium derivative In water; toluene; benzene for 2h;	100%
Stage #1: diphenylamine With Lithium dimsyl In tetrahydrofuran at 0℃; for 0.5h; Stage #2: carbon disulfide In tetrahydrofuran at 0 - 20℃; for 12h; Reagent/catalyst;	98%
With n-butyllithium 1) hexane, -78 deg C to RT, 2) -78 deg C to RT; Multistep reaction;
Stage #1: diphenylamine With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: carbon disulfide In tetrahydrofuran at 0 - 12℃; for 12h;
Stage #1: diphenylamine With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: carbon disulfide In tetrahydrofuran at 0 - 20℃; for 12h;

: 2375-30-6
pentafluorosulfanyl isocyanate

: 122-39-4
diphenylamine

: 90598-10-0
N'-(Pentafluorosulfanyl)-N,N-diphenylurea

Conditions

Conditions	Yield
In chloroform	100%

: 122-39-4
diphenylamine

: 61057-05-4
diphenylamine; deprotonated form

Conditions

Conditions	Yield
With NaH-cryptand<2.2.1> In tetrahydrofuran for 0.166667h;	100%

: 3972-65-4
1-bromo-4-tert-butylbenzene

: 122-39-4
diphenylamine

: 36809-23-1
N,N-diphenyl-N-(4-tert-butylphenyl)amine

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium tert-butylate In toluene at 20℃; for 4h;	100%
With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃;	96%
for 3h;	96%

: 122-39-4
diphenylamine

: 501-65-5
diphenyl acetylene

: 134414-84-9
((E)-1,2-Diphenyl-vinyl)-diphenyl-amine

Conditions

Conditions	Yield
phosphazene base-P4-tert-butyl In hexane; dimethyl sulfoxide at 120℃; for 24h;	100%

: 109-09-1
2-chloropyridine

: 122-39-4
diphenylamine

: 50910-08-2
2-N,N-diphenylaminopyridine

Conditions

Conditions	Yield
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); P(i-BuNCH2CH2)3N In toluene at 100℃; for 20h; Buchwald-Hartwig amination;	100%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;	99%

: 106-39-8
bromochlorobenzene

: 122-39-4
diphenylamine

: 4316-56-7
(p-chlorophenyl)diphenylamine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;	100%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃;	90.7%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 100℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	79%

: 122-39-4
diphenylamine

: 106-95-6
allyl bromide

: 65178-51-0
N-allyldiphenylamine

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile Reflux;	100%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile Reflux;	100%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 110℃; Inert atmosphere;	81%

: 18143-33-4
(chloromethyl)methoxydimethylsilane

: 122-39-4
diphenylamine

: N-{[dimethyl(methoxy)silyl]methyl}-N',N'-diphenyl-urea

Conditions

Conditions	Yield
In toluene at 80℃; for 2h;	100%

: 122-39-4
diphenylamine

: 2051-62-9
4'-biphenyl chloride

: 4432-94-4
N,N-bis(phenyl)-4-biphenylamine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;	100%
Stage #1: diphenylamine; 4'-biphenyl chloride With palladium diacetate; sodium sulfate; sodium t-butanolate; XPhos for 1h; Buchwald-Hartwig Coupling; Milling; Stage #2: In water; ethyl acetate for 0.0333333h; Reagent/catalyst; Buchwald-Hartwig Coupling; Milling;	51%

: 122-39-4
diphenylamine

: C12H10N(1-)*K(1+)*0.5C4H8O

Conditions

Conditions	Yield
With potassium hydride In tetrahydrofuran at 50℃; for 6h; Schlenk technique; Inert atmosphere;	100%

: 38460-95-6
undec-10-enoyl chloride

: 122-39-4
diphenylamine

: 52007-57-5
N,N-diphenylundec-10-enamide

Conditions

Conditions	Yield
In toluene for 3h; Reflux; Inert atmosphere;	100%

: 121281-53-6
hydrogen tetrakis(3,5-bis(trifluoromethyl)phenyl)borate

: 122-39-4
diphenylamine

: C12H11N*H(1+)*C32H12BF24(1-)

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 1h; Glovebox; Inert atmosphere;	100%

: 5394-63-8
2,2,6-trimethyl-4H-1,3-dioxin-4-one

: 122-39-4
diphenylamine

: 2540-31-0
N,N-diphenylacetoacetamide

Conditions

Conditions	Yield
In toluene at 20℃; for 12.25h; Reflux;	100%

: 1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene

: 122-39-4
diphenylamine

: C32H42N2

Conditions

Conditions	Yield
In pentane at 20℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique;	100%

: 869085-78-9
(5R,6S,9R)-2-(2,6-diisopropylphenyl)-6-isopropyl-3,3,9-trimethyl-2-azaspiro[4.5]decan-1-ylidene

: 122-39-4
diphenylamine

: C39H54N2

Conditions

Conditions	Yield
In pentane at 20℃; for 0.5h; Inert atmosphere; Glovebox;	100%

Diphenylamine Chemical Properties

Molecule structure of Diphenylamine (CAS NO.122-39-4):

IUPAC Name: N-Phenylaniline
Molecular Weight: 169.22244 g/mol
Molecular Formula: C₁₂H₁₁N
Melting Point: 52 °C
Index of Refraction: 1.634
Molar Refractivity: 55.62 cm³
Molar Volume: 155.4 cm³
Surface Tension: 44 dyne/cm
Density: 1.088 g/cm³
Flash Point: 152.8 °C
Enthalpy of Vaporization: 54.22 kJ/mol
Boiling Point: 302 °C at 760 mmHg
Vapour Pressure: 0.00102 mmHg at 25 °C
Storage Temp.: 0-6 °C
Water Solubility: slightly soluble. 0.03 g/100 mL
XLogP3: 3.5
H-Bond Donor: 1
H-Bond Acceptor: 1
Rotatable Bond Count: 2
Exact Mass: 169.089149
MonoIsotopic Mass: 169.089149
Topological Polar Surface Area: 12
Heavy Atom Count: 13
Canonical SMILES: C1=CC=C(C=C1)NC2=CC=CC=C2
InChI: InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChIKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N
EINECS: 204-539-4
Product Categories: Intermediates of Dyes and Pigments;Organics;Bridged diphenylsPesticides&Metabolites;Alpha sort;DAlphabetic;ACS GradeNitrogen Compounds;C11 to C38;Essential Chemicals;Routine Reagents;Nitrogen Compounds;76/768/EEC Annex VIII;Bridged diphenylsAlphabetic;DIO - DIZCosmetics;Other AdditivesEuropean Community: ISO and DIN;Proposed Banning;Allergens;D;Fungicides;Pesticides;Amines;Aromatics;Chemical Class;Derivatization Reagents TLC;Nitrogen-containing compoundsTitration;Redox IndicatorsDerivatization Reagents TLC;TLC Reagents, D-F;Indicators;TLC Visualization Reagents (alphabetic sort);TLC Visualization Reagents (by application)

Diphenylamine Uses

Diphenylamine (CAS NO.122-39-4) has anti-scald activity which protect the apple skin from the oxidation products of alpha-farnesene during storage. So Diphenylamine is used as a pre-or postharvest scald inhibitor for apples. The derivatives of Diphenylamine are useful in many ways. Ring-alkylated derivatives of diphenylamine are used as "antiozinates" in the manufacture of rubber products. The compound undergoes various cyclisaton reactions. It gives phenothiazine, a precursor to certain pharmaceuticals with sulfur.

Diphenylamine Production

Diphenylamine is manufactured by the thermal deamination of aniline over oxide catalysts:
2 C₆H₅NH₂ → (C₆H₅)₂NH + NH₃

Diphenylamine Toxicity Data With Reference

1.	orl-rat LD50:2 g/kg	GISAAA Gigiena i Sanitariya. 41 (5)(1976),21.
2.	orl-mus LD50:1750 mg/kg	GISAAA Gigiena i Sanitariya. 41 (5)(1976),21.
3.	orl-gpg LD50:300 mg/kg	FMCHA2 Farm Chemicals Handbook .(Meister Publishing,Willoughy, OH.: )1983,C85.

Diphenylamine Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Diphenylamine Safety Profile

Hazard Codes: Toxic T, Dangerous N, Flammable F
Risk Statements: 23/24/25-33-50/53-52/53-39/23/24/25-11
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R33:Danger of cumulative effects.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39:Danger of very serious irreversible effects.
R11:Highly flammable.
Safety Statements: 28-36/37-45-60-61-28A-16-7
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S16:Keep away from sources of ignition.
S7:Keep container tightly closed.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: JJ7800000
F: 8-10-23
HazardClass: 6.1
PackingGroup: III
Poison by ingestion. Experimental teratogenic effects. Action similar to aniline but less severe. Combustible when exposed to heat or flame. Can react violently with hexachloromelamine or trichloromelamine. Can react with oxidizing materials. To fight fire, use CO₂, dry chemical. When heated to decomposition it emits highly toxic fumes of NO_x. See also ANILINE, AMINES, and AROMATIC AMINES.

Diphenylamine Standards and Recommendations

OSHA PEL: TWA 10 mg/m³
ACGIH TLV: TWA 10 mg/m³; Not Classifiable as a Human Carcinogen

Diphenylamine Analytical Methods

For occupational chemical analysis use OSHA: #22.

Diphenylamine Specification

Diphenylamine (CAS NO.122-39-4) is also named as AI3-00781 ; Aniline, N-phenyl- ; Anilinobenzene ; Benzenamine, N-phenyl- ; Benzene, (phenylamino)- ; Benzene, anilino- ; Big Dipper ; C.I. 10355 ; CCRIS 4699 ; CI 10355 ; Caswell No. 398 ; DFA ; DPA (VAN) ; Deccoscald 282 ; Difenylamin ; Difenylamin [Czech] ; HSDB 1108 ; N,N-Diphenylamine ; N-Fenylanilin ; N-Fenylanilin [Czech] ; N-Phenylaniline ; N-Phenylbenzenamine ; NSC 215210 ; Naugalube 428L ; No-Scald ; No-Scald DPA 283 ; Phenylaniline ; Scaldip ; Shield DPA . Diphenylamine (CAS NO.122-39-4) is white crystals or powder with a pleasant odor. Dust may be explosive if mixed with air in critical proportions and in the presence of a source of ignition. Inhalation may irritate mucous membranes. Overexposure, including ingestion of solid or skin contact, may cause fast pulse, hypertension, and bladder trouble. Contact with dust irritates eyes. Diphenylamine discolors in light. It can react violently with hexachloromelamine and trichloromelamine. Diphenylamine is incompatible with strong oxidizing agents and strong acids. It is also incompatible with iron and silver salts. Diphenylamine reacts with nitrogen oxides.

Product Name

Diphenylamine

Synthetic route

Diphenylamine Chemical Properties

Diphenylamine Uses

Diphenylamine Production

Diphenylamine Toxicity Data With Reference

Diphenylamine Consensus Reports

Diphenylamine Safety Profile

Diphenylamine Standards and Recommendations

Diphenylamine Analytical Methods

Diphenylamine Specification

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