chlorobenzene
N-phenylphenylene-1,4-diamine
N,N'-diphenyl-1,4-phenylenediamine
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% |
dimethanesulfonate hydroquinone
aniline
N,N'-diphenyl-1,4-phenylenediamine
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% |
N4-(2-methylphenyl) benzene-1,4-diamine
N-phenylphenylene-1,4-diamine
phenol
A
N,N'-diphenyl-1,4-phenylenediamine
B
N-phenyl-N'-tolyl-p-phenylenediamine
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon In cyclohexanone at 250℃; for 6h; Autoclave; Inert atmosphere; | A 94.4% B 88.8% |
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon In cyclohexanone at 220℃; for 6h; Concentration; Autoclave; Inert atmosphere; | 93.6% |
Conditions | Yield |
---|---|
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃; | 92% |
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 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% |
malononitrile
A
2-(2,5-bis(phenylamino)phenyl)malononitrile
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
ethyl 2-cyanoacetate
A
ethyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
methyl 2-cyanoacetate
A
methyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
1-butanethiol
N,N'-diphenyl-1,4-phenylenediamine
A
C22H24N2S
B
C26H32N2S2
C
N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 6h; | A 74% B 10% C 11% |
acetylacetone
A
3-(2,5-bis(phenylamino)phenyl)pentane-2,4-dione
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
cyanoacetic acid tert-butyl ester
A
t-butyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
nitromethane
A
2-(nitromethyl)-N,N'-diphenyl-1,4-phenylenediamine
B
N,N'-diphenyl-1,4-phenylenediamine
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% |
Nitroethane
A
2-(1-nitroethyl)-N1,N4-diphenylbenzene-1,4-diamine
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
2-nitropropane
A
N1,N4-diphenyl-2-(prop-1-en-2-yl)benzene-1,4-diamine
B
N,N'-diphenyl-1,4-phenylenediamine
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 |
bromobenzene
N-phenylphenylene-1,4-diamine
N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; | 67% |
1,4-cyclohexanedione-2,5-dicarboxylic acid
aniline
N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
In various solvent(s) at 73℃; for 150h; | 53% |
Conditions | Yield |
---|---|
palladium In 5,5-dimethyl-1,3-cyclohexadiene; cyclohexanone; nitrobenzene | 40% |
cyclohexanone
4-nitro-aniline
A
4-ntrophenyl(phenyl)amine
B
N,N'-diphenyl-1,4-phenylenediamine
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% |
N,N'-diphenyl-1,4-phenylenediamine
N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
With zinc |
Conditions | Yield |
---|---|
With hydrogenchloride at 300℃; | |
With ammonium chloride at 300℃; |
N,N'-diphenyl-1,4-phenylenediamine
aniline
A
N,N'-diphenyl-1,4-phenylenediamine
B
azophenin
Conditions | Yield |
---|---|
at 220℃; unter Druck; |
Conditions | Yield |
---|---|
With sodium hydrogen sulfate at 200℃; | |
With hydrogenchloride at 300℃; | |
With phosphoric acid at 260℃; |
Conditions | Yield |
---|---|
With hydrogenchloride at 290℃; |
ethanol
N,N'-diphenyl-1,4-phenylenediamine
hydroquinone
A
N,N'-diphenyl-1,4-phenylenediamine
B
quinhydrone
Conditions | Yield |
---|---|
With ethanol |
2,2,4-trimethyl-6-hydroxy-1,2-dihydroquinoline
N,N'-diphenyl-1,4-phenylenediamine
A
2,2,4-trimethyl-6-oxo-2,6-dihydroquinoline
B
N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
In chlorobenzene at 23℃; Rate constant; Kinetics; other temps.; |
N,N'-diphenyl-1,4-phenylenediamine
acetic anhydride
N1-[4-methyl(phenyl)carboxamidophenyl]-N1-phenylacetamide
Conditions | Yield |
---|---|
With sodium acetate | 100% |
With sodium acetate at 120 - 130℃; for 3h; | 97% |
N,N'-diphenyl-1,4-phenylenediamine
A
N,N'-diphenyl-1,4-phenylenediamine
B
benzene-1,2-dicarboxylic acid
Conditions | Yield |
---|---|
With monoperoxyphthalic acid In tetrahydrofuran at 25℃; | A 88% B 98% |
Conditions | Yield |
---|---|
In xylene at reflux 140-106°C for 165 h, then distilling butanol-borane azeotrop; | A 98% B n/a |
formaldehyd
N,N'-diphenyl-1,4-phenylenediamine
N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
With NaBH4CN; acetic acid at 20℃; for 2.5h; Methylation; reduction; | 97% |
N,N'-diphenyl-1,4-phenylenediamine
<1,4>benzothiazino<2,3-b>phenothiazine
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; |
N,N'-diphenyl-1,4-phenylenediamine
N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.416667h; | 95% |
Conditions | Yield |
---|---|
With potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 120℃; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube; | 95% |
2-Picolinic acid
Terpinolene
3-Iodotoluene
N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
With potassium carbonate In nitrogen; water; ethyl acetate; toluene | 94.9% |
N,N'-diphenyl-1,4-phenylenediamine
methyl iodide
N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: N,N'-diphenyl-1,4-phenylenediamine With methyllithium at -78℃; Stage #2: methyl iodide at -60℃; | 94% |
N,N'-diphenyl-1,4-phenylenediamine
potassium acrylate
N-neopentyl-4-(4-methylpiperidinyl)-pyridinium chloride
3-Chloropropyltrimethoxysilan
3-(trimethoxysilyl)propyl acrylate
Conditions | Yield |
---|---|
In methanol | 92.7% |
1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride
N,N'-diphenyl-1,4-phenylenediamine
sodium methacrylate
3-Chloropropyltrimethoxysilan
γ-methacryl-oxypropyl-trimethoxysilane
Conditions | Yield |
---|---|
90.3% |
N,N'-diphenyl-1,4-phenylenediamine
4-N,N-diphenylamino-1-bromobenzene
1-N,1-N,4-N-triphenyl-4-N-[4-(N-[4-(N-phenylanilino)phenyl]anilino)phenyl]benzene-1,4-diamine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 110℃; for 12h; Ullmann Condensation; | 87.9% |
N,N'-diphenyl-1,4-phenylenediamine
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; |
1-bromo-4-octylbenzene
N,N'-diphenyl-1,4-phenylenediamine
bis-N,N'-(4-octylphenyl)-bis-N,N'-phenyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 48h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
sulfuric acid Product distribution / selectivity; | 85% |
Conditions | Yield |
---|---|
With zinc(II) chloride for 0.0833333h; microwave irradiation; | 84% |
Conditions | Yield |
---|---|
With zinc(II) chloride for 0.0833333h; microwave irradiation; | 83% |
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% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; for 12h; regioselective reaction; | 82% |
N,N'-diphenyl-1,4-phenylenediamine
1-bromo-4-(2-(2-methoxyethoxy)ethoxy)benzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Reflux; | 81% |
N,N'-diphenyl-1,4-phenylenediamine
1,4-Cyclohexanedione
N,N,N',N'-tetraphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In toluene for 12h; Heating; | 80% |
N,N'-diphenyl-1,4-phenylenediamine
phenylacetyl chloride
N,N'-diphenyl-N,N'-bis(2-phenacetyl)phenylene-1,4-diamine
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 5h; Cooling with ice; | 80% |
In 1,4-dioxane Heating; | 61% |
N,N'-diphenyl-1,4-phenylenediamine
B
N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.5h; | A 20% B 80% |
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
1,4-bis(phenyl amino)Benzene (74-31-7) is used as antioxidants in rubber industry.
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 . |
Reported in EPA TSCA Inventory.
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 NOx.
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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