2-Nitrodiphenylamine supplier

Name
2-Nitrodiphenylamine
EINECS 204-348-6
CAS No. 119-75-5
Article Data127
CAS DataBase
Density 1.36 g/cm³
Solubility negligible
Melting Point 74-76 °C(lit.)
Formula C₁₂H₁₀N₂O₂
Boiling Point 353.7 °C at 760 mmHg
Molecular Weight 214.224
Flash Point 167.7 °C
Transport Information
Appearance red crystalline solid
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In N,N-dimethyl-formamide	98%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In ethylene glycol at 140℃; for 8h; Inert atmosphere;	83%

: 1516-58-1
o-azidonitrobenzene

: 119-75-5
2-nitro-N-phenylaniline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In benzene for 7h;	A 58% B 18%

...Expand

: 88-74-4
2-nitro-aniline

: 100-63-0
phenylhydrazine

: 119-75-5
2-nitro-N-phenylaniline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In benzene for 30h; irradiation;	A 16.2% B 20.1% C 48.2%

...Expand

: 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

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

...Expand

: 88-74-4
2-nitro-aniline

: 108-90-7
chlorobenzene

: 119-75-5
2-nitro-N-phenylaniline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 108-86-1
bromobenzene

: 552-32-9
o-nitroacetanilide

: 119-75-5
2-nitro-N-phenylaniline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;	100%
With platinum(IV) oxide; hydrogen In methanol	99%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 12h; Heating;	74%

2-Nitrodiphenylamine Chemical Properties

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):

2-Nitrodiphenylamine 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.

2-Nitrodiphenylamine 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.

2-Nitrodiphenylamine 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

2-Nitrodiphenylamine 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.

Product Name

2-Nitrodiphenylamine

Synthetic route

2-Nitrodiphenylamine Chemical Properties

2-Nitrodiphenylamine Uses

2-Nitrodiphenylamine Toxicity Data With Reference

2-Nitrodiphenylamine Safety Profile

2-Nitrodiphenylamine Specification

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