25781-92-4

Basic information

• Product Name: 5-CHLORO-2-NITRODIPHENYLAMINE
• Synonyms: Benzenamine, 5-chloro-2-nitro-N-phenyl-;TIMTEC-BB SBB003166;5-CHLORO-3-NITRODIPHENYLAMINE;5-CHLORO-2-NITRODIPHENYLAMINE;2-Anilino-4-chloronitrobenzene;5-Chloro-2-nitro-N-phenylaniline;N-Phenyl-2-nitro-5-chloroaniline;5-Chloro-2-nitrodiphenylamine,98%
• CAS NO: 25781-92-4
• Molecular Formula: C₁₂H₉ClN₂O₂
• Molecular Weight: 248.67
• EINECS: 247-261-9
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 25781-92-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 110-114 °C
• Boiling Point: 370.414 °C at 760 mmHg
• Flash Point: 177.82 °C
• Appearance: orange-red fine crystalline powder
• Density: 1.3696 (rough estimate)
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Very Slightly, Heated)
• PKA: -4.38±0.50(Predicted)
• CAS DataBase Reference: 5-CHLORO-2-NITRODIPHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-NITRODIPHENYLAMINE(25781-92-4)
• EPA Substance Registry System: 5-CHLORO-2-NITRODIPHENYLAMINE(25781-92-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 25781-92-4(Hazardous Substances Data)

Usage

Chemical Properties

orange-red fine crystalline powder

Uses

Different sources of media describe the Uses of 25781-92-4 differently. You can refer to the following data:
1. 5-Chloro-2-nitrodiphenylaMine can be used in the preparation of substituted Phenylbenzimidazoles.
2. Reagent used in the preparation of substituted Phenylbenzimidazoles.

InChI:InChI=1/C12H9ClN2O2/c13-9-6-7-12(15(16)17)11(8-9)14-10-4-2-1-3-5-10/h1-8,14H

Synthetic route

4-chloro-2-fluoro-nitrobenzene (700-37-8) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
In dimethyl sulfoxide at 110℃; for 4h;	98%
With triethylamine In dimethyl sulfoxide at 20℃; for 43h;
With potassium carbonate In dimethyl sulfoxide at 50℃;
With potassium carbonate In dimethyl sulfoxide at 50℃;

3,4-dinitro-chlorobenzene (610-40-2) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
In ethanol at 20℃; for 10h; Solvent; Temperature; Time;	90%

4-chlorobenzonitrile (100-00-5) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
Stage #1: aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0166667h; Inert atmosphere; Stage #2: 4-chlorobenzonitrile In tetrahydrofuran; hexane at -78 - 110℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium permanganate; ammonia In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere;	49%

sodium acetate (127-09-3) + 3,4-dinitro-chlorobenzene (610-40-2) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

3,4-dinitro-chlorobenzene (610-40-2) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4) + aniline yellow (60-09-3)

Conditions	Yield
anschl. mit HCl;

3,4-dinitro-chlorobenzene (610-40-2) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4) + Phenyl azide (622-37-7)

2,4-dichloronitrobenzene (611-06-3) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
With sodium acetate

3,4-dinitro-chlorobenzene (610-40-2) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
With aniline In ethanol
With aniline In ethanol

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + trimethyl orthoformate (149-73-5) → 6-chloro-1-phenyl-1H-benzimidazole (96048-77-0)

Conditions	Yield
With hydrogen; pyridinium p-toluenesulfonate; palladium on activated charcoal In ethyl acetate at 20℃; under 2585.74 Torr; for 6h;	100%

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → 4-chloro-N2-phenylbenzene-1,2-diamine (68406-47-3)

Conditions	Yield
With hydrogen; platinum In methanol at 75 - 80℃; for 1.5h; Reagent/catalyst; Temperature; Solvent; Autoclave;	99.2%
With hydrogen In tetrahydrofuran; water at 120℃; under 37503.8 Torr; for 15h; chemoselective reaction;	94%
With ammonium chloride; zinc In methanol; water at 25 - 60℃;	84%

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + 1-Bromo-2-butyne (3355-28-0) → But-2-ynyl-(5-chloro-2-nitro-phenyl)-phenyl-amine (198839-48-4)

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

3-chloro-3-oxopropanoic acid methyl ester (37517-81-0) + 5-chloro-2-nitro-N-phenylaniline (25781-92-4) → C16H13ClN2O5

Conditions	Yield
Stage #1: 3-chloro-3-oxopropanoic acid methyl ester; 5-chloro-2-nitro-N-phenylaniline With triethylamine In toluene at 60 - 70℃; for 8h; Industrial scale; Stage #2: In acetonitrile at 20℃; Reflux; Industrial scale;	95.2%

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + ethyl chlorocarbonylacetate (36239-09-5) → ethyl 2-(N-(5-chloro-2-nitrophenyl)-N-phenylamino)formylacetate (22316-45-6)

Conditions	Yield
In acetonitrile for 12h; Reflux; Large scale;	91%
With 4-pyrrolidin-1-ylpyridine In acetonitrile at 80℃;

carbon monoxide (201230-82-2) + 5-chloro-2-nitro-N-phenylaniline (25781-92-4) → 4-chloro-N2-phenylbenzene-1,2-diamine (68406-47-3) + 6-chloro-1,3-dihydro-1-phenyl-2H-benzimidazol-2-one (54986-47-9)

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; sodium chloride In acetonitrile at 220℃; under 37503 Torr; for 2h;	A 10% B 90%

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + N-butylamine (109-73-9) → 4-butylamino-2-(phenylamino)nitrobenzene (182061-28-5)

Conditions	Yield
With potassium carbonate; potassium bromide at 100℃;	84%

hydrogen ethyl malonate (1071-46-1) + 5-chloro-2-nitro-N-phenylaniline (25781-92-4) → ethyl 2-(N-(5-chloro-2-nitrophenyl)-N-phenylamino)formylacetate (22316-45-6)

Conditions	Yield
With phosphorus pentachloride at 20℃; Reagent/catalyst; Reflux;	80%
With phosphorus pentachloride; sodium carbonate In xylene-petroleum ether; benzene

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + propargyl bromide (106-96-7) → (5-Chloro-2-nitro-phenyl)-phenyl-prop-2-ynyl-amine (198839-47-3)

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 4h; Heating;	72%

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + 1-bromo-3-phenylprop-2-yne (1794-48-5) → (5-Chloro-2-nitro-phenyl)-phenyl-(3-phenyl-prop-2-ynyl)-amine (198839-49-5)

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In benzene for 4h; Heating;	65%

1H-imidazole (288-32-4) + 5-chloro-2-nitro-N-phenylaniline (25781-92-4) → 4-1H-imidazolyl-2-phenylaminonitrobenzene (182061-30-9)

Conditions	Yield
With potassium carbonate; potassium bromide at 100℃;	58%

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → (5-chloro-2-nitro-phenyl)-nitroso-phenyl-amine

Conditions	Yield
With potassium nitrite; acetic acid man giesst die gelb gewordene Fluessigkeit in Wasser;

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + acetic anhydride (108-24-7) → N-(5-chloro-2-nitro-phenyl)-N-phenyl-acetamide (861342-91-8)

Conditions	Yield
With zinc(II) chloride

ethyl 2-(chlorosulfonyl)acetate (55896-93-0) + 5-chloro-2-nitro-N-phenylaniline (25781-92-4) → [(5-Chloro-2-nitro-phenyl)-phenyl-sulfamoyl]-acetic acid ethyl ester (61154-60-7)

Conditions	Yield
In xylene Heating;

5-chloro-2-nitro-N-phenylaniline (25781-92-4) + ethanolamine (141-43-5) → 2-(4-Nitro-3-phenylamino-phenylamino)-ethanol (182061-26-3)

Conditions	Yield
With potassium carbonate; potassium bromide at 100℃;

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → (5-ethoxy-2-nitro-phenyl)-phenyl-amine (93758-68-0) + 4.4'-diethoxy-2.2'-dianilino-azoxybenzene;6-nitro-3-oxy-diphenylamine

Conditions	Yield
With ethanol; sodium at 120℃; und man versetzt des Reaktionsprodukts mit Wasser;

(5-ethoxy-2-nitro-phenyl)-phenyl-amine (93758-68-0) + 5-chloro-2-nitro-N-phenylaniline (25781-92-4) → 4-nitro-3-(phenylamino)phenol + 4.4'-diethoxy-2.2'-dianilino-azoxybenzene;6-nitro-3-ethoxy-diphenylamine

Conditions	Yield
With ethanol; sodium at 120℃; und man versetzt des Reaktionsprodukts mit Wasser;

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → bis-(4-ethoxy-2-anilino-phenyl)-diazene-N-oxide + 4-nitro-3-anilino-phenol and 4-nitro-3-anilino-phenol-ethyl ether

Conditions	Yield
With ethanol; sodium at 120℃;

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → 4-Chloro-N2-phenyl-N2-prop-2-ynyl-benzene-1,2-diamine (198839-56-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / 50percent aq. NaOH, PhCH2(Et)3N+Br- / benzene / 4 h / Heating 2: 98 percent / 37percent aq.HCl, gl.AcOH, SnCl2*2H2O, Zn / 4 h / Ambient temperature View Scheme

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → N2-But-2-ynyl-4-chloro-N2-phenyl-benzene-1,2-diamine (198839-57-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 50percent aq. NaOH, PhCH2(Et)3N+Br- / benzene / 4 h / Heating 2: 95 percent / 37percent aq.HCl, gl.AcOH, SnCl2*2H2O, Zn / 4 h / Ambient temperature View Scheme

5-chloro-2-nitro-N-phenylaniline (25781-92-4) → (2-Azido-5-chloro-phenyl)-phenyl-prop-2-ynyl-amine (198839-69-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / 50percent aq. NaOH, PhCH2(Et)3N+Br- / benzene / 4 h / Heating 2: 98 percent / 37percent aq.HCl, gl.AcOH, SnCl2*2H2O, Zn / 4 h / Ambient temperature 3: 1.) NaNO2, 12 M aq.HCl, 2.) NaN3 / 1.) 0 deg C, 3 min, 2.) diethyl ether, 2 h View Scheme

Upstream product

• 108-86-1 bromobenzene 
• 1635-61-6 5-chloro-2-nitroaniline 
• 100-00-5 4-chlorobenzonitrile 
• 62-53-3 aniline 
• 700-37-8 4-chloro-2-fluoro-nitrobenzene 
• 610-40-2 3,4-dinitro-chlorobenzene 
• 611-06-3 2,4-dichloronitrobenzene 
• 127-09-3 sodium acetate 

Downstream Products

• 861342-91-8 N-(5-chloro-2-nitro-phenyl)-N-phenyl-acetamide 
• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 54986-47-9 6-chloro-1,3-dihydro-1-phenyl-2H-benzimidazol-2-one 
• 22316-45-6 ethyl 2-(N-(5-chloro-2-nitrophenyl)-N-phenylamino)formylacetate 
• 198839-49-5 (5-Chloro-2-nitro-phenyl)-phenyl-(3-phenyl-prop-2-ynyl)-amine 
• 93758-68-0 (5-ethoxy-2-nitro-phenyl)-phenyl-amine 
• 36985-45-2 8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one 
• 22316-47-8 clobazam 
• 1329991-47-0 C₂₀H₂₁ClN₄O 
• 1329990-25-1 C₁₇H₁₃ClN₄O 
• 1329990-87-5 C₁₇H₁₃ClN₄O 
• 1267635-28-8 C₁₈H₁₅ClN₄O 
• 1267634-98-9 C₂₀H₂₀ClN₃O₃ 
• 198839-71-3 (2-Azido-5-chloro-phenyl)-phenyl-(3-phenyl-prop-2-ynyl)-amine 

Relevant articles and documents

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The compound according to claim 1, wherein the compound is represented by the following Formula. The present invention relates to a composition for an organic optoelectric device, an organic optoelectric device, and a display device. The details of Formula 1 are as defined in the specification.

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