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119-75-5

Basic Information
CAS No.: 119-75-5
Name: Benzenamine,2-nitro-N-phenyl-
Article Data: 127
Cas Database
Molecular Structure:
Molecular Structure of 119-75-5 (Benzenamine,2-nitro-N-phenyl-)
Formula: C12H10N2O2
Molecular Weight: 214.224
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: N/A
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%
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    Product Name: 2-Nitrodiphenylamine CAS: 119-75-5 MF: C12H10N2O2 MW: 214.22 EINECS: 204-348-6 Mol File: 119-75-5.mol 2-Nitrodiphenylamine Structure 2-Nitrodiphenylamine Chemical Properties Melting point 74-76 °C(lit.) Boili

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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.