N,N'-Diphenyl-1,4-phenylenediamine supplier

Name
N,N-Diphenyl-p-phenylenediamine
EINECS 200-806-4
CAS No. 74-31-7
Article Data64
CAS DataBase
Density 1.2
Solubility insoluble AUTOIGNITION

Melting Point 145 - 152 C

Formula C18H16 N2

Boiling Point 220 - 225 C

Molecular Weight 260.338

Flash Point 297 °C

Transport Information 25kgs

Appearance light gray to brown powder

Safety 2215944

Risk Codes R43;R52/53

Molecular Structure

Hazard Symbols

Synonyms 1,4-Benzenediamine,N,N'-diphenyl- (9CI); p-Phenylenediamine, N,N'-diphenyl- (8CI);1,4-Bis(phenylamino)benzene; 1,4-Dianilinobenzene;4,4'-Diphenyl-p-phenylenediamine; 4-Phenylaminodiphenylamine; AgeRite DPPD;Altofane DIP; Antage DP; Antigen P; Antigene P; Antioxidant H; DFFD; DPPD;Diafen FF; Diafen FF-T; Diphenyl-p-phenylenediamine; Ekaland DPPD; Flexamine G;JZF; N,N'-Diphenyl-1,4-benzenediamine; N,N'-Diphenyl-1,4-phenylenediamine;N,N'-Diphenyl-p-phenylenediamine; NSC 5761; Naugard J; Nocrac DP; Nonflex H;Nonox DPPD; Permanax 18; Permanax DPPD; Stabilizer DPPD;p-Bis(phenylamino)benzene; p-Phenylaminodiphenylamine

PSA 24.06000

LogP 5.31980

Synthetic route

108-90-7
chlorobenzene

101-54-2
N-phenylphenylene-1,4-diamine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; chemoselective reaction; 99%

With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium t-butanolate In toluene at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; chemoselective reaction; 87%

126150-65-0
dimethanesulfonate hydroquinone

62-53-3
aniline

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

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%

66311-46-4
N4-(2-methylphenyl) benzene-1,4-diamine

101-54-2
N-phenylphenylene-1,4-diamine

108-95-2
phenol

A

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

B

27173-16-6
N-phenyl-N'-tolyl-p-phenylenediamine

Conditions

Conditions Yield

With 5%-palladium/activated carbon In cyclohexanone at 250℃; for 6h; Autoclave; Inert atmosphere; A 94.4%
B 88.8%

...Expand

101-54-2
N-phenylphenylene-1,4-diamine

108-95-2
phenol

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With 5%-palladium/activated carbon In cyclohexanone at 220℃; for 6h; Concentration; Autoclave; Inert atmosphere; 93.6%

108-90-7
chlorobenzene

106-50-3
1,4-phenylenediamine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃; 92%

106-37-6
1.4-dibromobenzene

62-53-3
aniline

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With potassium hydroxide In N,N-dimethyl-formamide at 130℃; for 0.55h; Buchwald-Hartwig Coupling; 91%

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0)

106-39-8
bromochlorobenzene

62-53-3
aniline

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With dicyclohexyl(2-methoxy-6-methylbiphenyl-2,-yl)phosphine; potassium tert-butylate; palladium diacetate In 1,4-dioxane at 160℃; for 0.5h; Inert atmosphere; Microwave irradiation; 86%

N,N' diphenyl-1,4 benzoquinone diimine

109-77-3
malononitrile

A

1200190-23-3
2-(2,5-bis(phenylamino)phenyl)malononitrile

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: malononitrile With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 80%
B n/a

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

105-56-6
ethyl 2-cyanoacetate

A

1200190-29-9
ethyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: ethyl 2-cyanoacetate With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 77%
B n/a

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

105-34-0
methyl 2-cyanoacetate

A

1200190-26-6
methyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: methyl 2-cyanoacetate With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 76%
B n/a

...Expand

109-79-5
1-butanethiol

6246-98-6, 73334-88-0, 73334-89-1
N,N'-diphenyl-1,4-phenylenediamine

A

911110-01-5
C22H24N2S

B

911110-02-6
C26H32N2S2

C

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

In tetrahydrofuran at 20℃; for 6h; A 74%
B 10%
C 11%

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

123-54-6
acetylacetone

A

1200190-20-0
3-(2,5-bis(phenylamino)phenyl)pentane-2,4-dione

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: acetylacetone With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 74%
B n/a

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

1116-98-9
cyanoacetic acid tert-butyl ester

A

1200190-32-4
t-butyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: cyanoacetic acid tert-butyl ester With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 73%
B n/a

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

75-52-5
nitromethane

A

1200190-10-8
2-(nitromethyl)-N,N'-diphenyl-1,4-phenylenediamine

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: nitromethane With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 72%
B 20%

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

79-24-3
Nitroethane

A

1200190-13-1
2-(1-nitroethyl)-N1,N4-diphenylbenzene-1,4-diamine

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: Nitroethane With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 70%
B n/a

...Expand

N,N' diphenyl-1,4 benzoquinone diimine

79-46-9
2-nitropropane

A

1200190-17-5
N1,N4-diphenyl-2-(prop-1-en-2-yl)benzene-1,4-diamine

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: 2-nitropropane With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere; A 68%
B n/a

...Expand

108-86-1
bromobenzene

101-54-2
N-phenylphenylene-1,4-diamine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; 67%

490-93-7
1,4-cyclohexanedione-2,5-dicarboxylic acid

62-53-3
aniline

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

In various solvent(s) at 73℃; for 150h; 53%

101-54-2
N-phenylphenylene-1,4-diamine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

palladium In 5,5-dimethyl-1,3-cyclohexadiene; cyclohexanone; nitrobenzene 40%

108-94-1
cyclohexanone

100-01-6
4-nitro-aniline

A

836-30-6
4-ntrophenyl(phenyl)amine

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With styrene; 10 wt% Pd(OH)2 on carbon In 1,4-dioxane at 150℃; under 3750.38 Torr; for 12h; Flow reactor; A 29%
B 6%

...Expand

6246-98-6, 73334-88-0, 73334-89-1
N,N'-diphenyl-1,4-phenylenediamine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With zinc

123-30-8
4-amino-phenol

62-53-3
aniline

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With hydrogenchloride at 300℃;

With ammonium chloride at 300℃;

106-37-6
1.4-dibromobenzene

118-92-3
anthranilic acid

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

6246-98-6, 73334-88-0, 73334-89-1
N,N'-diphenyl-1,4-phenylenediamine

62-53-3
aniline

A

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

B

4435-12-5
azophenin

...Expand

51-78-5
p-aminophenol hydrochloride

62-53-3
aniline

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

at 220℃; unter Druck;

62-53-3
aniline

123-31-9
hydroquinone

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With sodium hydrogen sulfate at 200℃;

With hydrogenchloride at 300℃;

With phosphoric acid at 260℃;

62-53-3
aniline

106-50-3
1,4-phenylenediamine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With hydrogenchloride at 290℃;

64-17-5
ethanol

6246-98-6, 73334-88-0, 73334-89-1
N,N'-diphenyl-1,4-phenylenediamine

123-31-9
hydroquinone

A

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

B

106-34-3
quinhydrone

...Expand

156-10-5
p-nitrosodiphenylamine

100-63-0
phenylhydrazine

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With ethanol

72107-05-2
2,2,4-trimethyl-6-hydroxy-1,2-dihydroquinoline

6246-98-6, 73334-88-0, 73334-89-1
N,N'-diphenyl-1,4-phenylenediamine

A

4071-18-5
2,2,4-trimethyl-6-oxo-2,6-dihydroquinoline

B

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

In chlorobenzene at 23℃; Rate constant; Kinetics; other temps.;

...Expand

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

108-24-7
acetic anhydride

113510-51-3
N1-[4-methyl(phenyl)carboxamidophenyl]-N1-phenylacetamide

Conditions

Conditions Yield

With sodium acetate 100%

With sodium acetate at 120 - 130℃; for 3h; 97%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

A

6246-98-6, 73334-88-0, 73334-89-1
N,N'-diphenyl-1,4-phenylenediamine

B

88-99-3
benzene-1,2-dicarboxylic acid

Conditions

Conditions Yield

With monoperoxyphthalic acid In tetrahydrofuran at 25℃; A 88%
B 98%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

7330-48-5
dibutoxyphenylborane

A

BN(C6H5)C6H4N(C6H5)

B

71-36-3
butan-1-ol

Conditions

Conditions Yield

In xylene at reflux 140-106°C for 165 h, then distilling butanol-borane azeotrop; A 98%
B n/a

...Expand

50-00-0
formaldehyd

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

17754-68-6
N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With NaBH4CN; acetic acid at 20℃; for 2.5h; Methylation; reduction; 97%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

111385-12-7
<1,4>benzothiazino<2,3-b>phenothiazine

Conditions

Conditions Yield

With iodine; sulfur at 180℃; for 24h; 95%

Stage #1: N,N'-diphenyl-1,4-phenylenediamine With iodine; sulfur at 180 - 200℃; Inert atmosphere;
Stage #2: With sodium sulfide for 2h; Reflux; 64.3%

With iodine; sulfur

With hydrogen sulfide; iodine; sulfur; phenylhydrazine 1.) o-dichlorobenzene, reflux, 24 h 2.) 150 deg C; Yield given. Multistep reaction;

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

2716-09-8
N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine

Conditions

Conditions Yield

With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.416667h; 95%

623-00-7
4-bromobenzenecarbonitrile

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

C32H22N4

Conditions

Conditions Yield

With potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 120℃; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube; 95%

98-98-6
2-Picolinic acid

copper(ll) sulfate pentahydrate

586-62-9
Terpinolene

625-95-6
3-Iodotoluene

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,4-phenylenediamine

Conditions

Conditions Yield

With potassium carbonate In nitrogen; water; ethyl acetate; toluene 94.9%

...Expand

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

74-88-4
methyl iodide

17754-68-6
N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

Stage #1: N,N'-diphenyl-1,4-phenylenediamine With methyllithium at -78℃;
Stage #2: methyl iodide at -60℃; 94%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

10192-85-5
potassium acrylate

95758-27-3
N-neopentyl-4-(4-methylpiperidinyl)-pyridinium chloride

2530-87-2
3-Chloropropyltrimethoxysilan

4369-14-6
3-(trimethoxysilyl)propyl acrylate

Conditions

Conditions Yield

In methanol 92.7%

...Expand

109911-78-6
1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

5536-61-8
sodium methacrylate

2530-87-2
3-Chloropropyltrimethoxysilan

7727-32-4
γ-methacryl-oxypropyl-trimethoxysilane

Conditions

Conditions Yield

90.3%

...Expand

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

36809-26-4
4-N,N-diphenylamino-1-bromobenzene

141546-10-3
1-N,1-N,4-N-triphenyl-4-N-[4-(N-[4-(N-phenylanilino)phenyl]anilino)phenyl]benzene-1,4-diamine

Conditions

Conditions Yield

With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 110℃; for 12h; Ullmann Condensation; 87.9%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

N,N’-diphenyl-p-benzoquinonediimine

Conditions

Conditions Yield

With 1,4-diaza-bicyclo[2.2.2]octane; copper diacetate In dichloromethane at 20℃; for 7h; 87%

With lead dioxide

With 4-(phenylimino)cyclohexa-2,5-dienone In chlorobenzene at 68.45℃; Equilibrium constant; Thermodynamic data; Further Variations:; Temperatures;

51554-93-9
1-bromo-4-octylbenzene

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

1257423-28-1
bis-N,N'-(4-octylphenyl)-bis-N,N'-phenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 48h; Inert atmosphere; 86%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

98-83-9
isopropenylbenzene

phenylenediamine derivative

phenylenediamine derivative

Conditions

Conditions Yield

sulfuric acid Product distribution / selectivity; 85%

4839-46-7
3,3-Dimethylglutaric acid

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

C25H20N2

Conditions

Conditions Yield

With zinc(II) chloride for 0.0833333h; microwave irradiation; 84%

110-94-1
1,5-pentanedioic acid

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

C23H16N2

Conditions

Conditions Yield

With zinc(II) chloride for 0.0833333h; microwave irradiation; 83%

6781-98-2
2,6-dimethyl-1-chlorobenzene

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

N,N'-bis(1,3-dimethylphenyl)-N,N'-diphenyl-1,4-phenylenediamine

Conditions

Conditions Yield

With bis(di-tert-butyl(2-butenyl)phosphine)dichloropalladium; sodium t-butanolate In o-xylene at 130 - 135℃; for 6h; Reagent/catalyst; Inert atmosphere; 82%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

4891-38-7
phenylpropynoic acid methyl ester

1,2-diphenyl-6-phenylamino-quinolin-4(1H)-one

Conditions

Conditions Yield

With trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; for 12h; regioselective reaction; 82%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

112968-89-5
1-bromo-4-(2-(2-methoxyethoxy)ethoxy)benzene

C40H44N2O6

Conditions

Conditions Yield

With tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Reflux; 81%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

637-88-7
1,4-Cyclohexanedione

14118-16-2
N,N,N',N'-tetraphenyl-p-phenylenediamine

Conditions

Conditions Yield

toluene-4-sulfonic acid In toluene for 12h; Heating; 80%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

103-80-0
phenylacetyl chloride

351424-85-6
N,N'-diphenyl-N,N'-bis(2-phenacetyl)phenylene-1,4-diamine

Conditions

Conditions Yield

With pyridine In chloroform at 20℃; for 5h; Cooling with ice; 80%

In 1,4-dioxane Heating; 61%

74-31-7
N,N'-diphenyl-1,4-phenylenediamine

A

C18H15N3O

B

2716-09-8
N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine

Conditions

Conditions Yield

With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.5h; A 20%
B 80%

N,N'-Diphenyl-1,4-phenylenediamine Chemical Properties

Chemical Name: N,N-Diphenyl-p-phenylenediamine
IUPAC NAME: 1-N,4-N-Diphenylbenzene-1,4-diamine
CAS No.: 74-31-7
EINECS: 200-806-4
RTECS: ST2275000
Molecular Formula: C₁₈H₁₆N₂
Molecular Weight: 260.33 g/mol
Melting Point: 143-145 °C(lit.)
Density: 1.175 g/cm³
Flash Point: 297 °C
Boiling Point: 469.2 °C at 760 mmHg
Storage temp.: 2-8°C
Following is the structure of 1,4-bis(phenyl amino)Benzene (74-31-7):

Product Categories about 1,4-bis(phenyl amino)Benzene (74-31-7) are Organics ; Diphenylamines (for High-Performance Polymer Research) ; Functional Materials ; Reagent for High-Performance Polymer Research
The chemical synonymous of 1,4-bis(phenyl amino)Benzene (74-31-7) are 4,4'-Diphenyl-p-phenylenediamine ; 4-Phenylaminodiphenylamine ; Altofane Dip ; Altofanedip ; Antage Dp ; Antagedp ; Antigenep

N,N'-Diphenyl-1,4-phenylenediamine Uses

1,4-bis(phenyl amino)Benzene (74-31-7) is used as antioxidants in rubber industry.

N,N'-Diphenyl-1,4-phenylenediamine Toxicity Data With Reference

1.
eye-rbt 500 mg/24H SEV
    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,73.

2.
mma-sat 10 µg/plate
    PCBRD2    Progress in Clinical and Biological Research. 141 (1984),407.

3.
msc-ham:lng 30 mg/L
    SWEHDO    Scandinavian Journal of Work, Environment and Health. 9 (Suppl 2)(1983),27.

4.
orl-rat LD50:2370 mg/kg
    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,73.

5.
orl-mus LD50:18 g/kg
    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 10 (3)(1966),49.

6.
ipr-mus LD50:300 mg/kg
    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .

N,N'-Diphenyl-1,4-phenylenediamine Consensus Reports

Reported in EPA TSCA Inventory.

N,N'-Diphenyl-1,4-phenylenediamine Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A weak allergen. Experimental teratogenic and reproductive effects. An eye irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes:
Xi: Irritant
Risk Statements about 1,4-bis(phenyl amino)Benzene (74-31-7):
R 43 May cause sensitization by skin contact.
R 52/53 Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements about 1,4-bis(phenyl amino)Benzene (74-31-7):
S 24 Avoid contact with skin.
S 37 Wear suitable gloves.
S 61 Avoid release to the environment. Refer to special instructions/safety data sheets.
Attentions:
1. Storage: Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
2. Handling: All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.

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Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; chemoselective reaction;	99%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium t-butanolate In toluene at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; chemoselective reaction;	87%

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 130℃; for 0.55h; Buchwald-Hartwig Coupling;	91%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0)

Conditions	Yield
With hydrogenchloride at 300℃;
With ammonium chloride at 300℃;

Conditions	Yield
With sodium hydrogen sulfate at 200℃;
With hydrogenchloride at 300℃;
With phosphoric acid at 260℃;

Conditions	Yield
With sodium acetate	100%
With sodium acetate at 120 - 130℃; for 3h;	97%

Conditions	Yield
With iodine; sulfur at 180℃; for 24h;	95%
Stage #1: N,N'-diphenyl-1,4-phenylenediamine With iodine; sulfur at 180 - 200℃; Inert atmosphere; Stage #2: With sodium sulfide for 2h; Reflux;	64.3%
With iodine; sulfur
With hydrogen sulfide; iodine; sulfur; phenylhydrazine 1.) o-dichlorobenzene, reflux, 24 h 2.) 150 deg C; Yield given. Multistep reaction;

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; copper diacetate In dichloromethane at 20℃; for 7h;	87%
With lead dioxide
With 4-(phenylimino)cyclohexa-2,5-dienone In chlorobenzene at 68.45℃; Equilibrium constant; Thermodynamic data; Further Variations:; Temperatures;

Conditions	Yield
With pyridine In chloroform at 20℃; for 5h; Cooling with ice;	80%
In 1,4-dioxane Heating;	61%

1.	eye-rbt 500 mg/24H SEV	28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,73.
2.	mma-sat 10 µg/plate	PCBRD2 Progress in Clinical and Biological Research. 141 (1984),407.
3.	msc-ham:lng 30 mg/L	SWEHDO Scandinavian Journal of Work, Environment and Health. 9 (Suppl 2)(1983),27.
4.	orl-rat LD50:2370 mg/kg	28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,73.
5.	orl-mus LD50:18 g/kg	GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 10 (3)(1966),49.
6.	ipr-mus LD50:300 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .

Product Name

N,N-Diphenyl-p-phenylenediamine

Synthetic route

N,N'-Diphenyl-1,4-phenylenediamine Chemical Properties

N,N'-Diphenyl-1,4-phenylenediamine Uses

N,N'-Diphenyl-1,4-phenylenediamine Toxicity Data With Reference

N,N'-Diphenyl-1,4-phenylenediamine Consensus Reports

N,N'-Diphenyl-1,4-phenylenediamine Safety Profile

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