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Basic Information
| CAS No.: | 119-75-5 |
|---|---|
| Name: | 2-Nitrodiphenylamine |
| Article Data: | 127 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-37/39 |
| PSA: | 57.85000 |
| LogP: | 3.93460 |
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Synthetic route
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% |
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% |
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% |
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% |
Conditions
| Conditions | Yield |
|---|---|
| With potassium fluoride In dimethyl sulfoxide at 130℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere; | 98% |
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% |
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. |
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% |
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% |
Conditions
| Conditions | Yield |
|---|---|
| copper In dichloromethane for 20h; Ambient temperature; | 90% |
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2-Nitrodiphenylamine
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):
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.
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.
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
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.
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.