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119-75-5

Basic Information
CAS No.: 119-75-5
Name: Benzenamine,2-nitro-N-phenyl-
Molecular Structure:
Molecular Structure of 119-75-5 (Benzenamine,2-nitro-N-phenyl-)
Formula: C12H10N2O2
Molecular Weight: 214.22
Synonyms: Diphenylamine,2-nitro- (8CI);2-Nitro-N-phenylaniline;C.I. 10335;N-Phenyl-2-nitroaniline;N-Phenyl-2-nitrobenzenamine;N-Phenyl-o-nitroaniline;NSC 105613;NSC 4754;NSC 629274;Sudan Yellow 1339;o-(Phenylamino)nitrobenzene;o-Nitro-N-phenylaniline;o-Nitrodiphenylamine;
EINECS: 204-348-6
Density: 1.36 g/cm3
Melting Point: 74-76 °C(lit.)
Boiling Point: 353.7 °C at 760 mmHg
Flash Point: 167.7 °C
Solubility: negligible
Appearance: red crystalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 57.85000
LogP: 3.93460
Synthetic route
62-53-3

aniline

342589-38-2

2-nitrophenyl nonaflate

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 115℃; for 0.75h; microwave irradiation;99%
With potassium phosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 105℃; for 13h;97%
108-86-1

bromobenzene

88-74-4

2-nitro-aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;98%
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 30h; Ullmann condensation;90%
With copper(l) iodide; potassium carbonate; pipecolic Acid In N,N-dimethyl-formamide at 110℃; for 24h; Ullmann cross-coupling reaction;87%
577-19-5

2-nitrophenyl bromide

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃;98%
With potassium hydroxide In water at 20℃; for 6h; Green chemistry;78%
With C30H24N3OPPd at 120℃; for 24h; Inert atmosphere; Alkaline conditions;75%
62-53-3

aniline

1493-27-2

ortho-nitrofluorobenzene

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
In N,N-dimethyl-formamide98%
With triethylamine In neat (no solvent) at 140℃; for 9h;96%
Stage #1: aniline With sodium hydride In tetrahydrofuran; mineral oil for 0.25h;
Stage #2: ortho-nitrofluorobenzene In tetrahydrofuran; mineral oil at 75℃; for 1h;
94%
5570-19-4

2-nitrophenylboronic acid

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With potassium fluoride In dimethyl sulfoxide at 130℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;98%
1484-35-1

N-acetyl-N-phenyl-o-nitroaniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 3.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating;96%
609-73-4

o-nitroiodobenzene

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With C30H24N3OPPd at 120℃; for 24h; Inert atmosphere; Alkaline conditions;96%
With toluene-4-sulfonic acid at 165℃; for 0.833333h; Ionic liquid; Microwave irradiation;79%
With palladium bis(2,2,6,6-tetramethyl-3,5-heptanedione); potassium tert-butylate In toluene at 120℃; for 40h; Inert atmosphere;68 %Chromat.
88-73-3

2-Chloronitrobenzene

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 8h; Inert atmosphere; Green chemistry;93%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 80℃; for 1h;86%
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; Solvent; Inert atmosphere; Sealed tube;86%
62-53-3

aniline

528-29-0

1,2-Dinitrobenzene

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
Stage #1: aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0166667h; Inert atmosphere;
Stage #2: 1,2-Dinitrobenzene In tetrahydrofuran; hexane at -120 - -110℃; for 0.166667h; Inert atmosphere;
Stage #3: With potassium permanganate; ammonia In tetrahydrofuran; hexane at -110℃; for 0.0833333h; Inert atmosphere;
90%
28899-97-0

triphenylbismuth(V) diacetate

88-74-4

2-nitro-aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
copper In dichloromethane for 20h; Ambient temperature;90%
591-50-4

iodobenzene

88-74-4

2-nitro-aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With iron(III) chloride; caesium carbonate; copper(II) oxide; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;89%
With CuMoO4; caesium carbonate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;73%
With copper(l) iodide; cesium acetate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;63%
33948-36-6

2-iodocyclohex-2-en-1-one

88-74-4

2-nitro-aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 75℃; for 8h; Inert atmosphere;85%
98-80-6

phenylboronic acid

612-29-3

o-nitronitrosobenzene

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With triethyl phosphite In toluene at 20℃; for 0.75h;85%
13091-23-1

4-chloro-3-nitropyridine

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
In ethylene glycol at 140℃; for 8h; Inert atmosphere;83%
1516-58-1

o-azidonitrobenzene

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With boron trifluoride In benzene at 50℃; for 6h;82%
88-74-4

2-nitro-aniline

98-80-6

phenylboronic acid

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With copper(II)(1,1′-di(2-picolyl)-3,3′-methylenedibenzimidazolium) dihexafluorophosphate In methanol at 20℃;79%
With potassium acetate In N,N-dimethyl-formamide at 20℃; for 15h;73%
With C37H35NiO2P2S2(1+)*F6P(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 10h; Chan-Lam Coupling;65%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃;45 %Chromat.
865-47-4

potassium tert-butylate

586-96-9

Nitrosobenzene

A

119-75-5

2-nitro-N-phenylaniline

B

28548-57-4

N-(4-nitrosophenyl)-N-phenylhydroxylamine

Conditions
ConditionsYield
In benzene for 7h;A 58%
B 18%
88-74-4

2-nitro-aniline

100-63-0

phenylhydrazine

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With copper phthalocyanine; copper diacetate; acetic acid at 25℃;55%
With tetrabenzoporphyrinatocobalt(II); copper diacetate In acetonitrile at 0℃; for 13h; chemoselective reaction;30%
62-53-3

aniline

15163-59-4

potassium o-nitrobenzoate

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With copper(II) sulfate In 1-methyl-pyrrolidin-2-one at 140℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere;52%
21565-15-1

N-nitroso(2-nitrophenyl)phenylamine

A

119-75-5

2-nitro-N-phenylaniline

B

18264-71-6

bis(2-nitrophenyl)amine

C

612-36-2

2-nitro-N-(4-nitrophenyl)benzenamine

Conditions
ConditionsYield
In benzene for 30h; irradiation;A 16.2%
B 20.1%
C 48.2%
4597-87-9

2-(N-methylamino)pyridine

98-95-3

nitrobenzene

A

836-30-6

4-ntrophenyl(phenyl)amine

B

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With oxygen; sodium t-butanolate In dimethyl sulfoxide at 20℃; for 1h;A 36%
B 10%
88-74-4

2-nitro-aniline

108-90-7

chlorobenzene

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 48h; Ullmann condensation;32%
With copper(l) iodide; potassium carbonate; pipecolic Acid In N,N-dimethyl-formamide at 110℃; for 36h; Ullmann cross-coupling reaction;31%
With palladium bis(2,2,6,6-tetramethyl-3,5-heptanedione); potassium tert-butylate In toluene at 120℃; for 40h; Inert atmosphere;23 %Chromat.
103-71-9

phenyl isocyanate

88-74-4

2-nitro-aniline

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With potassium carbonate In nitrobenzene at 190℃; for 4h;10%
382165-80-2

N-nitrosodiphenylamine

A

836-30-6

4-ntrophenyl(phenyl)amine

B

119-75-5

2-nitro-N-phenylaniline

C

122-39-4

diphenylamine

Conditions
ConditionsYield
In benzene for 30h; irradiation; 860 and 900 react un the same way;A 5.3%
B 2.2%
C 6.2%
In benzene for 30h; irradiation;A 5.3%
B 2.2%
C 6.2%
108-86-1

bromobenzene

552-32-9

o-nitroacetanilide

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate und folgendes Verseifen mit warmer konzentrierter Salzsaeure;
21565-15-1

N-nitroso(2-nitrophenyl)phenylamine

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With sulfuric acid
With 2,3,3,4,4,5-hexamethyl-2-hexanethiol In methanol Quantum yield; Irradiation; other solvents, other concentrations, other reagents;0.018 mg
76476-05-6

2-nitrodiphenylamine-4-sulfonic acid

119-75-5

2-nitro-N-phenylaniline

Conditions
ConditionsYield
With hydrogenchloride at 130 - 140℃;
64-17-5

ethanol

88-73-3

2-Chloronitrobenzene

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

31515-43-2

1-nitro-2-(phenylsulfonyl)benzene

62-53-3

aniline

119-75-5

2-nitro-N-phenylaniline

119-75-5

2-nitro-N-phenylaniline

534-85-0

N-phenyl-1,2-benzenediamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;100%
With platinum(IV) oxide; hydrogen In methanol99%
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;99%
119-75-5

2-nitro-N-phenylaniline

74-88-4

methyl iodide

52997-62-3

2-nitro-N-methyl-N-phenylaniline

Conditions
ConditionsYield
Stage #1: 2-nitro-N-phenylaniline With potassium hydroxide In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;64%
With sodium hydride 1.) DMF, 1 h, 2.) DMF, 1 h; Multistep reaction;
119-75-5

2-nitro-N-phenylaniline

benzene 1,3,5-triyl triformate

14813-85-5

1-phenyl-1,3-dihydrobenzoimidazol-2-one

Conditions
ConditionsYield
With selenium; triethylamine In N,N-dimethyl-formamide at 120℃; Inert atmosphere; Sealed tube;99%
119-75-5

2-nitro-N-phenylaniline

870-63-3

prenyl bromide

C17H18N2O2

C17H18N2O2

Conditions
ConditionsYield
Stage #1: 2-nitro-N-phenylaniline With sodium hydride; triethylamine In 1,2-dimethoxyethane at 0℃;
Stage #2: prenyl bromide In 1,2-dimethoxyethane at 20℃; Further stages.;
97%
119-75-5

2-nitro-N-phenylaniline

3355-28-0

1-Bromo-2-butyne

198839-45-1

But-2-ynyl-(2-nitro-phenyl)-phenyl-amine

Conditions
ConditionsYield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 4h; Heating;96%
1458-98-6

2-methyl-3-bromo-1-propene

119-75-5

2-nitro-N-phenylaniline

181861-36-9

N-(2-nitrophenyl)-N-(2-methylprop-2-enyl)aniline

Conditions
ConditionsYield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 12h; Heating;95%
64-18-6

formic acid

119-75-5

2-nitro-N-phenylaniline

2622-60-8

1-phenyl-1H-benzoimidazole

Conditions
ConditionsYield
With iron; ammonium chloride In isopropyl alcohol at 80℃; for 2h;94%
With palladium 10% on activated carbon; triethylamine at 150℃; for 0.0833333h; Microwave irradiation;86%
119-75-5

2-nitro-N-phenylaniline

106-95-6

allyl bromide

181861-34-7

N-(2-nitrophenyl)-N-(prop-2-enyl)aniline

Conditions
ConditionsYield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 12h; Heating;91%
67-56-1

methanol

119-75-5

2-nitro-N-phenylaniline

2622-60-8

1-phenyl-1H-benzoimidazole

Conditions
ConditionsYield
With iron; ammonium chloride at 68 - 70℃; for 48h; Inert atmosphere;91%
With Pt-TiO2 at 32℃; for 4h; UV-irradiation; Inert atmosphere;40 %Chromat.
119-75-5

2-nitro-N-phenylaniline

100-51-6

benzyl alcohol

2622-67-5

1,2-diphenyl-1H-benzoimidazole

Conditions
ConditionsYield
With 2 mol-% Pd/C; potassium tert-butylate In chlorobenzene at 80℃; for 4h; Inert atmosphere;87%
119-75-5

2-nitro-N-phenylaniline

31438-22-9

1-nitro-9H-carbazole

Conditions
ConditionsYield
With oxygen; tin(II) acetate; palladium(II) trifluoroacetate In acetic acid at 116℃; for 50h; Cyclization; Aromatic ring closure;80%
119-75-5

2-nitro-N-phenylaniline

35826-31-4

3-amino-4-(phenylamino)pyridine

Conditions
ConditionsYield
With iron; ammonium chloride In ethylene glycol for 2h; Inert atmosphere; Reflux;80%
119-75-5

2-nitro-N-phenylaniline

92-82-0

Phenazin

Conditions
ConditionsYield
With triphenylphosphine for 0.0583333h; Cadogan reaction; Microwave irradiation;75%
With triphenylphosphine In toluene at 250℃; for 0.166667h; Sealed tube;38%
With potassium hydroxide; aniline; xylene
119-75-5

2-nitro-N-phenylaniline

106-96-7

propargyl bromide

181861-73-4

(2-Nitro-phenyl)-phenyl-prop-2-ynyl-amine

Conditions
ConditionsYield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 12h; Heating;74%
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    bulk production Product Name: 2-Nitrodiphenylamine purity:99%min Molecular formula: C12H10N2O2 Molecular weight: 214.22 CAS No: 119-75-5 Other names: 2 - NITRO - N - PHENYLANILINE Appearance:Orange-Red Powder Storage:Dry and ventilat

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    2-Nitrodiphenylamine

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    Orange-red flake or crystalline powder 98%min 2-Nitrodiphenylamine CAS NO 119-75-5 Best pice&High quality Timely despatch Appearance:Orange-red flake or crystalline powder Storage:Keep in a cool, dry, dark location in a tightly sealed conta

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    2-Nitrodiphenylamine

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Chemistry

2-Nitrodiphenylamine(119-75-5), also called NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline, or N-phenyl-o-nitroaniline, is an organic chemical, a nitrated aromatic amine, a derivate of diphenylamine. Its chemical formula is C12H10N2O2, or C6H5NHC6H4NO2. It is a red crystalline solid, usually in form of flakes or powder, with melting point of 74-76 °C and boiling point of 346 °C. It is polar but hydrophobic. Its CAS number is 119-75-5.
The molecular structure of 2-Nitrodiphenylamine(119-75-5):

Uses

2-Nitrodiphenylamine(119-75-5) is used as a stabilizer for synthetic rubbers, explosives, propellants (eg. in Otto fuel II, smokeless powders, in some US Army double-base propellants in solid rockets, and in other applications involving nitric acid esters), plastics, and lubricants. It is also an intermediate for organic synthesis, and a civilian solvent dye.
In some explosives, it is used to control the explosion. One of its major uses is to control the explosion rate of propylene glycol dinitrate.
As a stabilizer, its major role is to eliminate the acidic nitrates and nitrogen oxides produced by gradual decomposition of nitric acid esters, which would otherwise autocatalyze further decomposition. Its amount is usually 1-2% of the mixture; higher amounts than 2% degrade the propellant's ballistic properties. The amount of the stabilizer depletes with time; remaining content of less than 0.5% (with initial 2% content) requires increased surveillance of the munition, with less than 0.2% warranting immediate disposal, as the depletion of the stabilizer may lead to autoignition of the propellant.

Toxicity Data With Reference

RTECS#: CAS# 119-75-5: None listed
LD50/LC50: RTECS: Not available. Other: Oral, rat: LD50 > 3200 mg/kg 
Carcinogenicity: 2-Nitrodiphenylamine - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated.

Safety Profile

Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-37/39
WGK Germany  3
Hazard Note  Irritant
HS Code  29214400

Specification

Chemical Stability: Stable under normal temperatures and pressures. 
Conditions to Avoid: High temperatures, incompatible materials. 
Incompatibilities with Other Materials Strong oxidizing agents, strong acids.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide. 
Hazardous Polymerization Has not been reported.