119-75-5

Basic information

• Product Name: 2-Nitrodiphenylamine
• Synonyms: LABOTEST-BB LT00053209;c.i. 10335;O-NITRO DIPHENYLAMINE;TIMTEC-BB SBB000544;Sudan Yellow 1339;2-nitro-n-phenyl-benzenamin;Benzenamine,2-nitro-N-phenyl-;Diphenylamine, 2-nitro-
• CAS NO: 119-75-5
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• EINECS: 204-348-6
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;API intermediates;Aromatics Compounds;Aromatics;Amine series;Amines;Building Blocks;C12;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;amine| nitro-compound
• Mol File: 119-75-5.mol
• Article Data: 96

Chemical Properties

• Melting Point: 74-76 °C(lit.)
• Boiling Point: 346 °C
• Flash Point: 346°C
• Appearance: red crystalline solid
• Density: 1.36
• Vapor Density: 10.7 (vs air)
• Vapor Pressure: 4.83E-06mmHg at 25°C
• Refractive Index: 1.6660 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), , DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: -3.39±0.20(Predicted)
• Water Solubility: negligible
• BRN: 2213591
• CAS DataBase Reference: 2-Nitrodiphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrodiphenylamine(119-75-5)
• EPA Substance Registry System: 2-Nitrodiphenylamine(119-75-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 119-75-5(Hazardous Substances Data)

Usage

Description

2-Nitrodiphenylamine is a double-base (DB) rocket propellant stabilizer and its microencapsulation potentially improves the shelf life of DB rocket propellants.

Chemical Properties

Red Crystalline Solid

Uses

Different sources of media describe the Uses of 119-75-5 differently. You can refer to the following data:
1. (2-Nitrophenyl)phenylamine (cas# 119-75-5) is a compound useful in organic synthesis.
2. 2-Nitrodiphenylamine is used to control the combustion of propylene glycol dinitrate in Otto fuel II (US navy propellant for torpedoes and other weapons systems); Also used as a solvent dye; Used as stabilizer for nitroglycerin and as a chemical intermediate

General Description

Red-brown crystalline powder or reddish-brown solid.

Air & Water Reactions

2-Nitrodiphenylamine may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2-Nitrodiphenylamine is incompatible with strong oxidizers, strong acids and strong bases.

Health Hazard

Symptoms of exposure to this chemical include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Structurally similar chemicals may cause methemoglobinemia. ?ACUTE/CHRONIC HAZARDS: This chemical may be harmful by inhalation or ingestion. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides

Fire Hazard

Flash point data for 2-Nitrodiphenylamine are not available; however, 2-Nitrodiphenylamine is probably combustible.

Synthesis

The synthesis of 2-Nitrodiphenylamine is as follows:The mixture of phenylboronic acid (1 mmol), aromatic amine (1.2 mmol) and 0.12 g (2 mmol) of KF in DMSO (4 mL) were added to Cu-IS-AMBA-MNPs (0.06 g, 0.025 mmol) at 130 °C under nitrogen atmosphere for 2 h with vigorous stirring. Then, after completion of the reaction, the catalyst was separated by an external magnet and washed with dry CH2Cl2?three times and checked for its reusability. The solvent of the reaction mixture was evaporated by a rotary evaporator and then ethyl acetate and water were added to the residue. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using ethyl acetate/n-hexane.

InChI:InChI=1/C12H10N2O2/c13-11-7-6-10(8-12(11)14(15)16)9-4-2-1-3-5-9/h1-8H,13H2

Synthetic route

aniline (62-53-3) + 2-nitrophenyl nonaflate (342589-38-2) → 2-nitro-N-phenylaniline (119-75-5)

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%

bromobenzene (108-86-1) + 2-nitro-aniline (88-74-4) → 2-nitro-N-phenylaniline (119-75-5)

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%

2-nitrophenyl bromide (577-19-5) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

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%

aniline (62-53-3) + ortho-nitrofluorobenzene (1493-27-2) → 2-nitro-N-phenylaniline (119-75-5)

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%

2-nitrophenylboronic acid (5570-19-4) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

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

N-acetyl-N-phenyl-o-nitroaniline (1484-35-1) → 2-nitro-N-phenylaniline (119-75-5)

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%

o-nitroiodobenzene (609-73-4) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

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.

2-Chloronitrobenzene (88-73-3) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

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%

aniline (62-53-3) + 1,2-Dinitrobenzene (528-29-0) → 2-nitro-N-phenylaniline (119-75-5)

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%

triphenylbismuth(V) diacetate (28899-97-0) + 2-nitro-aniline (88-74-4) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
copper In dichloromethane for 20h; Ambient temperature;	90%

iodobenzene (591-50-4) + 2-nitro-aniline (88-74-4) → 2-nitro-N-phenylaniline (119-75-5)

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%

2-iodocyclohex-2-en-1-one (33948-36-6) + 2-nitro-aniline (88-74-4) → 2-nitro-N-phenylaniline (119-75-5)

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

phenylboronic acid (98-80-6) + o-nitronitrosobenzene (612-29-3) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
With triethyl phosphite In toluene at 20℃; for 0.75h;	85%

4-chloro-3-nitropyridine (13091-23-1) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

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

o-azidonitrobenzene (1516-58-1) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
With boron trifluoride In benzene at 50℃; for 6h;	82%

2-nitro-aniline (88-74-4) + phenylboronic acid (98-80-6) → 2-nitro-N-phenylaniline (119-75-5)

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.

potassium tert-butylate (865-47-4) + Nitrosobenzene (586-96-9) → 2-nitro-N-phenylaniline (119-75-5) + N-(4-nitrosophenyl)-N-phenylhydroxylamine (28548-57-4)

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

2-nitro-aniline (88-74-4) + phenylhydrazine (100-63-0) → 2-nitro-N-phenylaniline (119-75-5)

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%

aniline (62-53-3) + potassium o-nitrobenzoate (15163-59-4) → 2-nitro-N-phenylaniline (119-75-5)

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

N-nitroso(2-nitrophenyl)phenylamine (21565-15-1) → 2-nitro-N-phenylaniline (119-75-5) + bis(2-nitrophenyl)amine (18264-71-6) + 2-nitro-N-(4-nitrophenyl)benzenamine (612-36-2)

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

2-(N-methylamino)pyridine (4597-87-9) + nitrobenzene (98-95-3) → 4-ntrophenyl(phenyl)amine (836-30-6) + 2-nitro-N-phenylaniline (119-75-5)

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

2-nitro-aniline (88-74-4) + chlorobenzene (108-90-7) → 2-nitro-N-phenylaniline (119-75-5)

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.

phenyl isocyanate (103-71-9) + 2-nitro-aniline (88-74-4) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
With potassium carbonate In nitrobenzene at 190℃; for 4h;	10%

N-nitrosodiphenylamine (382165-80-2) → 4-ntrophenyl(phenyl)amine (836-30-6) + 2-nitro-N-phenylaniline (119-75-5) + diphenylamine (122-39-4)

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%

bromobenzene (108-86-1) + o-nitroacetanilide (552-32-9) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
With copper(l) iodide; potassium carbonate und folgendes Verseifen mit warmer konzentrierter Salzsaeure;

N-nitroso(2-nitrophenyl)phenylamine (21565-15-1) → 2-nitro-N-phenylaniline (119-75-5)

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

2-nitrodiphenylamine-4-sulfonic acid (76476-05-6) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
With hydrogenchloride at 130 - 140℃;

ethanol (64-17-5) + 2-Chloronitrobenzene (88-73-3) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

1-nitro-2-(phenylsulfonyl)benzene (31515-43-2) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

2-nitro-N-phenylaniline (119-75-5) → N-phenyl-1,2-benzenediamine (534-85-0)

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%

2-nitro-N-phenylaniline (119-75-5) + methyl iodide (74-88-4) → 2-nitro-N-methyl-N-phenylaniline (52997-62-3)

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;

2-nitro-N-phenylaniline (119-75-5) + benzene 1,3,5-triyl triformate → 1-phenyl-1,3-dihydrobenzoimidazol-2-one (14813-85-5)

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

2-nitro-N-phenylaniline (119-75-5) + prenyl bromide (870-63-3) → C17H18N2O2

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%

2-nitro-N-phenylaniline (119-75-5) + 1-Bromo-2-butyne (3355-28-0) → But-2-ynyl-(2-nitro-phenyl)-phenyl-amine (198839-45-1)

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 4h; Heating;	96%

2-methyl-3-bromo-1-propene (1458-98-6) + 2-nitro-N-phenylaniline (119-75-5) → N-(2-nitrophenyl)-N-(2-methylprop-2-enyl)aniline (181861-36-9)

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 12h; Heating;	95%

formic acid (64-18-6) + 2-nitro-N-phenylaniline (119-75-5) → 1-phenyl-1H-benzoimidazole (2622-60-8)

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%

2-nitro-N-phenylaniline (119-75-5) + allyl bromide (106-95-6) → N-(2-nitrophenyl)-N-(prop-2-enyl)aniline (181861-34-7)

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 12h; Heating;	91%

methanol (67-56-1) + 2-nitro-N-phenylaniline (119-75-5) → 1-phenyl-1H-benzoimidazole (2622-60-8)

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.

2-nitro-N-phenylaniline (119-75-5) + benzyl alcohol (100-51-6) → 1,2-diphenyl-1H-benzoimidazole (2622-67-5)

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

2-nitro-N-phenylaniline (119-75-5) → 1-nitro-9H-carbazole (31438-22-9)

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

2-nitro-N-phenylaniline (119-75-5) → 3-amino-4-(phenylamino)pyridine (35826-31-4)

Conditions	Yield
With iron; ammonium chloride In ethylene glycol for 2h; Inert atmosphere; Reflux;	80%

2-nitro-N-phenylaniline (119-75-5) → Phenazin (92-82-0)

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

2-nitro-N-phenylaniline (119-75-5) + propargyl bromide (106-96-7) → (2-Nitro-phenyl)-phenyl-prop-2-ynyl-amine (181861-73-4)

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

Upstream product

• 382165-80-2 N-nitrosodiphenylamine 
• 118-92-3 anthranilic acid 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 122-39-4 diphenylamine 
• 62-53-3 aniline 
• 7664-93-9 sulfuric acid 
• 21565-15-1 N-nitroso(2-nitrophenyl)phenylamine 
• 98-95-3 nitrobenzene 
• 102-07-8 bis(diphenyl)urea 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 88-74-4 2-nitro-aniline 
• 1484-35-1 N-acetyl-N-phenyl-o-nitroaniline 
• 27122-72-1 Hexakis-<2-nitro-phenoxy>-cyclotriphosphonitril 

Downstream Products

• 121613-97-6 2-(dimethylamino)-N-methyl-diphenylamine 
• 174181-40-9 N-(2-nitrophenyl)-N-phenylmalonamic acid methyl ester 
• 92-82-0 Phenazin 
• 41520-83-6 N,N'-bis-(2-nitro-phenyl)-benzidine 
• 2622-60-8 1-phenyl-1H-benzoimidazole 
• 1179813-43-4 N-hydroxy-7-(1-phenyl-1H-benzo[d]imidazol-2-yl)-heptanamide 
• 1449691-00-2 C₂₁H₂₄N₂O₂ 
• 1449690-82-7 C₂₁H₂₆N₂O₃ 
• 23996-36-3 1-methyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 2622-67-5 1,2-diphenyl-1H-benzoimidazole 
• 86-74-8 9H-carbazole 
• 35826-31-4 3-amino-4-(phenylamino)pyridine 
• 61154-59-4 [(2-Nitro-phenyl)-phenyl-sulfamoyl]-acetic acid ethyl ester 
• 61154-73-2 [(2-amino-phenyl)-phenyl-sulfamoyl]-acetic acid 

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