Conditions | Yield |
---|---|
With oxygen; sodium hydroxide In dimethyl sulfoxide at 60℃; for 4h; Reagent/catalyst; | 97.3% |
nitrobenzene
aniline
A
Phenazin
B
p-nitrosodiphenylamine
C
4-ntrophenyl(phenyl)amine
D
N-methylaniline
E
Azobenzene
Conditions | Yield |
---|---|
tetramethyl ammoniumhydroxide In water at 70 - 75℃; under 54.7555 Torr; for 3.5h; | A 1% B 87.9% C 6.9% D 1% E 6% |
nitrobenzene
aniline
A
Phenazin
B
p-nitrosodiphenylamine
C
4-ntrophenyl(phenyl)amine
D
Azobenzene
Conditions | Yield |
---|---|
betaine; tetramethyl ammoniumhydroxide In water at 70 - 75℃; under 54.7555 Torr; for 3.5h; | A 0.7% B 86.9% C 8.5% D 3.7% |
potassium hydroxide; dibenzo-18-crown-6; betaine at 80℃; under 54.7555 Torr; for 6h; | A 1.3% B 65% C 13.2% D 15.7% |
potassium hydroxide; betaine In water; isopropyl alcohol at 80℃; under 760.051 Torr; for 6h; | A 1.3% B 65.8% C 7.1% D 17.2% |
nitrobenzene
aniline
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
Conditions | Yield |
---|---|
Stage #1: aniline With potassium hydroxide at 60℃; under 45.0045 Torr; for 3h; Stage #2: nitrobenzene at 60℃; | A 76% B 20% |
With sodium hydroxide; tetramethyl ammoniumhydroxide; tetramethylammonium carbonate In ethanol at 75℃; for 5h; Product distribution / selectivity; | |
With sodium hydroxide; tetramethyl ammoniumhydroxide; water at 75℃; under 60.006 Torr; Conversion of starting material; |
nitrobenzene
aniline
A
Phenazin
B
p-nitrosodiphenylamine
C
4-ntrophenyl(phenyl)amine
D
Azobenzene
E
4-(Phenylazo)diphenylamine
Conditions | Yield |
---|---|
potassium hydroxide; betaine In methanol; water at 40 - 80℃; under 30.003 - 150.015 Torr; for 6h; | A 1.2% B 73.5% C 13.5% D 9.6% E 0.17% |
potassium hydroxide; betaine In methanol | A 1.1% B 58.6% C 12.8% D 13.2% E 0.2% |
potassium hydroxide; betaine In water at 80℃; under 19.502 - 397.54 Torr; for 5h; | A 1.25 %Chromat. B 35.7 %Chromat. C 17.8 %Chromat. D 10.9 %Chromat. E 0.12 %Chromat. |
nitrobenzene
Acetanilid
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
C
Azobenzene
Conditions | Yield |
---|---|
With sodium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; for 5h; | A 62% B 10% C 10% |
With sodium hydroxide In dimethyl sulfoxide at 80℃; for 5h; Mechanism; other solvent, other temperature; | A 60% B 10% C 10% |
With sodium hydroxide In dimethyl sulfoxide at 80℃; for 5h; | A 60% B 10% C 10% |
With sodium hydroxide In dimethyl sulfoxide at 130℃; for 5h; | A 30% B 10% C 30% |
nitrobenzene
bis(diphenyl)urea
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
C
Azobenzene
D
azoxybenzene
Conditions | Yield |
---|---|
With sodium hydroxide; tetramethyl ammoniumhydroxide In water at 80℃; under 50 - 90 Torr; for 3h; Product distribution / selectivity; | A 6% B 52% C 9% D 8% |
With potassium hydroxide; tetramethyl ammoniumhydroxide In water at 80℃; under 50 - 90 Torr; for 3h; Product distribution / selectivity; | A 3% B 38% C 3% D 10% |
Stage #1: nitrobenzene; bis(diphenyl)urea With sodium hydroxide; tetramethyl ammoniumhydroxide In water at 80℃; under 50 - 90 Torr; for 3h; Stage #2: With acetic acid In water; ethyl acetate Product distribution / selectivity; | A 6 %Chromat. B 52 - 85 %Chromat. C 9 - 10 %Chromat. D 8 - 17 %Chromat. |
Stage #1: nitrobenzene; bis(diphenyl)urea With potassium hydroxide; tetramethyl ammoniumhydroxide In water at 80℃; under 50 - 90 Torr; for 3h; Stage #2: With acetic acid In water; ethyl acetate Product distribution / selectivity; | A 3 %Chromat. B 38 %Chromat. C 3 %Chromat. D 10 %Chromat. |
nitrobenzene
bis(diphenyl)urea
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
C
azoxybenzene
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 80℃; under 760 Torr; for 3h; Product distribution / selectivity; | A 4% B 50% C 15% |
Stage #1: nitrobenzene; bis(diphenyl)urea With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 80℃; under 760 Torr; for 3h; Stage #2: With acetic acid In water; dimethyl sulfoxide; ethyl acetate Product distribution / selectivity; | A 4 %Chromat. B 50 %Chromat. C 15 %Chromat. |
nitrobenzene
aniline
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
C
Azobenzene
D
4-(Phenylazo)diphenylamine
Conditions | Yield |
---|---|
sodium hydroxide; betaine In methanol at 70℃; for 5h; | A 26.3% B 16.8% C 40.8% D 5.1% |
nitrobenzene
bis(diphenyl)urea
A
Phenazin
B
p-nitrosodiphenylamine
C
4-ntrophenyl(phenyl)amine
D
Azobenzene
E
azoxybenzene
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water at 70 - 100℃; under 50 - 90 Torr; for 3h; Product distribution / selectivity; | A 3% B 8% C 37% D 4% E 12% |
Stage #1: nitrobenzene; bis(diphenyl)urea With tetramethyl ammoniumhydroxide In water at 70 - 100℃; under 50 - 760 Torr; for 3h; Stage #2: With acetic acid In water; ethyl acetate Product distribution / selectivity; | A 0 - 8 %Chromat. B 3 - 9 %Chromat. C 29 - 90 %Chromat. D 0 - 10 %Chromat. E 0 - 27 %Chromat. |
nitrobenzene
aniline
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
C
Azobenzene
Conditions | Yield |
---|---|
potassium hydroxide; betaine at 70℃; | A 36% B 16.3% C 13.8% |
potassium hydroxide; betaine In methanol at 50 - 55℃; under 39.0039 Torr; for 4.5h; | A 18.2 %Chromat. B 10.0 %Chromat. C 8.5 %Chromat. |
lithium hydroxide; betaine at 70℃; | A 0.15% B 0.34% C 0.24% |
nitrobenzene
bis(diphenyl)urea
A
Phenazin
B
p-nitrosodiphenylamine
C
4-ntrophenyl(phenyl)amine
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water; toluene at 80℃; under 300 Torr; for 3h; Product distribution / selectivity; | A 2% B 9% C 35% |
Stage #1: nitrobenzene; bis(diphenyl)urea With tetramethyl ammoniumhydroxide In water; toluene at 80℃; under 300 - 760 Torr; for 3h; Stage #2: With acetic acid In water; ethyl acetate; toluene Product distribution / selectivity; | A 0 - 2 %Chromat. B 7 - 9 %Chromat. C 10 - 35 %Chromat. |
nitrobenzene
bis(diphenyl)urea
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water at 80℃; under 760 Torr; for 3h; Product distribution / selectivity; | A 3% B 29% |
With tetramethyl ammoniumhydroxide In water; toluene at 80℃; under 760 Torr; for 3h; Product distribution / selectivity; | A 7% B 10% |
With tetramethyl ammoniumhydroxide In tetrahydrofuran; water at 80℃; under 760 Torr; for 3h; Product distribution / selectivity; | A 3% B 9% |
Stage #1: nitrobenzene; bis(diphenyl)urea With tetramethyl ammoniumhydroxide In tetrahydrofuran; water at 80℃; under 760 Torr; for 3h; Stage #2: With acetic acid In tetrahydrofuran; water; ethyl acetate Product distribution / selectivity; | A 3 %Chromat. B 9 %Chromat. |
nitrobenzene
bis(diphenyl)urea
A
Phenazin
B
p-nitrosodiphenylamine
C
4-ntrophenyl(phenyl)amine
D
azoxybenzene
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water; benzene at 80℃; under 760 Torr; for 3h; Product distribution / selectivity; | A 2% B 10% C 24% D 5% |
Stage #1: nitrobenzene; bis(diphenyl)urea With tetramethyl ammoniumhydroxide In water; benzene at 80℃; under 760 Torr; for 3h; Stage #2: With acetic acid In water; ethyl acetate; benzene Product distribution / selectivity; | A 2 %Chromat. B 10 %Chromat. C 24 %Chromat. D 5 %Chromat. |
N-phenylquinone diimine
p-nitrosodiphenylamine
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride |
Conditions | Yield |
---|---|
With sodium hydroxide at 120 - 125℃; |
Conditions | Yield |
---|---|
With hydrogenchloride; methanol anschliessend Behandeln mit Natriumnitrit; | |
With hydrogenchloride; methanol; diethyl ether anschliessend Behandeln mit N-Nitroso-N-methyl-anilin in Aether; | |
With sulfuric acid; sodium nitrite |
N-nitrosodiphenylamine
p-nitrosodiphenylamine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 21℃; Rate constant; Mechanism; | |
With hydrogenchloride; ethanol Entsteht das salzsaure Salz; | |
With hydrogenchloride; ethanol man loest das sich ausscheidende salzsaure Salz in Natronlauge und behandelt der filtrierten Loesung mit CO2; |
aniline
A
p-nitrosodiphenylamine
B
4-ntrophenyl(phenyl)amine
C
trans-azobenzene
D
4-(Phenylazo)diphenylamine
E
N-phenylphenylene-1,4-diamine
Conditions | Yield |
---|---|
With dihydrogen peroxide In dimethyl sulfoxide for 24h; Product distribution; also N-methylaniline; | A 3.1 mmol B 19.7 mmol C 63 mmol D 1.1 mmol E 3.3 mmol |
Conditions | Yield |
---|---|
(i) MeOH, TsOH, (ii) /BRN= 605631/, aq. HCl; Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid |
hydrogenchloride
diethyl ether
ethanol
N-methyl-N-nitrosoaniline
diphenylamine
p-nitrosodiphenylamine
nitrobenzene
aniline
A
Phenazin
B
Phenazin-mono-N-Oxyd
C
p-nitrosodiphenylamine
D
Azobenzene
N-phenylquinone diimine
p-nitrosodiphenylamine
hydrogenchloride
nitroso-(4-nitroso-phenyl)-phenyl-amine
p-nitrosodiphenylamine
phenyl-bis-[4-(N-phenyl-hydrazino)-phenyl]-methane
acetic acid
p-nitrosodiphenylamine
Phenazin
p-nitrosodiphenylamine
4-ntrophenyl(phenyl)amine
Azobenzene
N-phenylphenylene-1,4-diamine
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol; water at 180℃; under 37503.8 Torr; for 0.116667h; | 99.1% |
p-nitrosodiphenylamine
acetic anhydride
N-{4[(acetyloxy)imino]-2,5-cyclohexadien-1-ylidene}aniline
Conditions | Yield |
---|---|
With pyridine In toluene at 5 - 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 92% |
With sodium hydroxide In water | 70% |
carbon disulfide
p-nitrosodiphenylamine
4-ntrophenyl(phenyl)amine
N-phenylphenylene-1,4-diamine
Conditions | Yield |
---|---|
With sulfur at 250℃; under 60006 Torr; for 4h; | 88% |
Conditions | Yield |
---|---|
With sodium hydroxide In acetonitrile at 5 - 20℃; for 2h; | 83.7% |
p-nitrosodiphenylamine
4-bromo-3-methyl-1-phenylpyrazol-5-one
C22H18N4O2
Conditions | Yield |
---|---|
In ethanol for 8h; Ambient temperature; | 72% |
3-amino-2-methyl-4-oxoquinazoline
p-nitrosodiphenylamine
2-Methyl-3-(4-phenylamino-phenyl-diazenyl)-3H-quinazolin-4-one
Conditions | Yield |
---|---|
With sodium acetate; acetic acid Heating; | 70% |
p-nitrosodiphenylamine
3-Amino-2-(n-butyl)quinazolin-4(3H)-one
2-Butyl-3-(4-phenylamino-phenyl-diazenyl)-3H-quinazolin-4-one
Conditions | Yield |
---|---|
With sodium acetate; acetic acid Heating; | 70% |
p-nitrosodiphenylamine
3-amino-2-phenylquinazolin-4(3H)-one
2-Phenyl-3-(4-phenylamino-phenyl-diazenyl)-3H-quinazolin-4-one
Conditions | Yield |
---|---|
With sodium acetate; acetic acid Heating; | 65% |
p-nitrosodiphenylamine
edaravone
3-methyl-1-phenyl-4-(p-phenylamino)phenylimino-2-pyrazolin-5-one
Conditions | Yield |
---|---|
at 110℃; for 0.333333h; | 46% |
p-nitrosodiphenylamine
N1,N3,N5-triphenylbenzene-1,3,5-triamine
10-phenyl-6,8-bis(phenylamino)-2,10-dihydrophenazin-2-one
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water for 3h; | 18% |
p-nitrosodiphenylamine
N1,N3,N5-triphenylbenzene-1,3,5-triamine
A
10-phenyl-6,8-bis(phenylamino)-2,10-dihydrophenazin-2-one
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water | A 18% B 11% |
5-methyl-benzo[b]thiophen-3-ol
p-nitrosodiphenylamine
Conditions | Yield |
---|---|
With ethanol |
IUPAC Name: 4-Nitroso-N-phenylaniline
Synonyms: 4-Nitroso-N-phenylaniline ; Benzenamine, 4-nitroso-N-phenyl- ; 4-Nitrosodiphenylamine ; 4-Nitroso-N-Phenylbenzenamine
Product Categories: Nitrogen Compounds;Nitroso Compounds;Organic Building Blocks
CAS NO: 156-10-5
Molecular Formula of p-Nitrosodiphenylamine (CAS NO.156-10-5) : C12H10N2O
Molecular Weight of p-Nitrosodiphenylamine (CAS NO.156-10-5) : 198.22
Molecular Structure of p-Nitrosodiphenylamine (CAS NO.156-10-5) :
EINECS: 205-848-7
Index of Refraction: 1.596
Surface Tension: 44.5 dyne/cm
Density: 1.12 g/cm3
Flash Point: 169.5 °C
Enthalpy of Vaporization: 60.2 kJ/mol
Boiling Point: 356.7 °C at 760 mmHg
Vapour Pressure: 2.86E-05 mmHg at 25°
Melting point: 144 °C (dec.)(lit.)
Appearance:Green plates with bluish luster or a black powder.
Water solubility:Insoluble in water.
Solubility: soluble in ethanol, ether, chloroform, benzene, slightly soluble in water.
P-Nitrosodiphenylamine (CAS NO.156-10-5) is used as rubber vulcanization accelerator.
Raw materials :CARBON DIOXIDE-->Diphenylamine
Preparation Products: 4-Aminodiphenylamine-->4-Aminodiphenylamine
Preparation of a p-Nitrosodiphenylamine by rearrangement of an N-Nitrosodiphenylamine at a temperature of from about 20°C to about 50°C. in the presence of Hydrogen chloride and a two solvent system comprising a water immiscible alcohol and an aromatic solvent having boiling points of from about 80°C to about 160°C.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 178mg/kg (178mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00267, |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 ,1982,p. 227.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-190 ,1979. . Community Right-To-Know List. Reported in EPA TSCA Inventory.
Poison by intravenous route. Suspected carcinogen with experimental carcinogenic and neoplastigenic data. Moderately toxic by ingestion. Mutation data reported. An eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also N-NITROSO COMPOUNDS and AMINES.
Hazard Codes Xn
Risk Statements 22-36/38
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
Safety Statements 26-36/37
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
RIDADR 2811
WGK Germany 3
RTECS JK0175000
HazardClass 6.1(b)
PackingGroup III
Reactivity Profile : 4-Nitrosodiphenylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. May react with strong oxidizing agents .
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