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

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

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-NITRODIPHENYLAMINE is used as a chemical intermediate for the preparation of substituted Phenylbenzimidazoles, which are important compounds in the development of pharmaceutical products. These substituted Phenylbenzimidazoles have potential applications in the treatment of various medical conditions due to their unique chemical structures and properties.
Used in Chemical Industry:
In the chemical industry, 5-CHLORO-2-NITRODIPHENYLAMINE serves as a reagent in the preparation of substituted Phenylbenzimidazoles. These substituted compounds are valuable for their diverse applications, including their use as dyes, pigments, and additives in various industrial processes. The versatility of 5-CHLORO-2-NITRODIPHENYLAMINE as a reagent makes it an essential component in the synthesis of a wide range of chemical products.

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

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

Downstream Products

• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 861342-91-8 N-(5-chloro-2-nitro-phenyl)-N-phenyl-acetamide 
• 61154-60-7 [(5-Chloro-2-nitro-phenyl)-phenyl-sulfamoyl]-acetic acid ethyl ester 
• 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 
• 182061-30-9 4-1H-imidazolyl-2-phenylaminonitrobenzene 
• 182061-26-3 2-(4-Nitro-3-phenylamino-phenylamino)-ethanol 
• 182061-28-5 4-butylamino-2-(phenylamino)nitrobenzene 
• 198839-48-4 But-2-ynyl-(5-chloro-2-nitro-phenyl)-phenyl-amine 
• 198839-47-3 (5-Chloro-2-nitro-phenyl)-phenyl-prop-2-ynyl-amine 
• 198839-49-5 (5-Chloro-2-nitro-phenyl)-phenyl-(3-phenyl-prop-2-ynyl)-amine 
• 96048-77-0 6-chloro-1-phenyl-1H-benzimidazole 
• 198839-56-4 4-Chloro-N²-phenyl-N²-prop-2-ynyl-benzene-1,2-diamine 
• 198839-57-5 N²-But-2-ynyl-4-chloro-N²-phenyl-benzene-1,2-diamine 

Relevant articles and documents

COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE

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.

A 1,5-benzodiazepine derivatives zhuo Tong method for the preparation of (by machine translation)

This invention relates to a kind of 1,5 the zhuo Tong[...] and method for preparing derivatives of nitrogen, characterized in that in order to replace the raw materials of dinitro compound is phthalic acid, with a substituted aniline reaction, the reaction with malonic acid monoester, then cyclization to obtain a target compound. The method step of this invention is simple, cheap material, easy to operate and achieve commercial, yield and purity are greatly improved. (by machine translation)

Oxidative nucleophilic aromatic amination of nitrobenzenes

Nitrobenzenes substituted with electron-acceptor groups such as halogen, nitro, trifluoromethyl, pentafluorosulfanyl, or cyano underwent oxidative nucleophilic substitution with lithium salts of arylamines to afford N-aryl-2-nitroanilines.

N2,N4-BIS(4-(PIPERAZINE-1-YL)PHENYL)PIRIMIDINE-2,4-DIAMINE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING CANCER

Disclosed herein are a new N2,N4-bis(4-(piperazin-1-yl)phenyl)pyrimidin-2,4-diamine derivative or a pharmaceutically acceptable salt thereof and a pharmaceutical composition for the prevention or treatment of cancers containing the same as an active ingredient. The compound of the present invention has excellent inhibitory effects against the activities of anaplastic lymphoma kinase (ALK) and activated cdc42-associated kinase (ACK1) and thus can improve the therapeutic effects on the treatment of cancer cells having anaplastic lymphoma kinase fusion proteins such as EML4-ALK and NPM-ALK, and also effectively prevent the recurrence of cancers thus being useful as a pharmaceutical composition for the prevention and treatment of cancers.

N2,N4-BIS(4-(PIPERAZINE-1-YL)PHENYL)PIRIMIDINE-2,4-DIAMINE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING CANCER

The present invention relates to a N2,N4-bis(4-(piperazine-1-yl)phenyl)pirimidine-2,4-diamine derivative or a pharmaceutically acceptable salt thereof, and to a composition containing same as an active ingredient for preventing or treating cancer. Since the compound according to the present invention has good effects in inhibiting the activities of anaplastic lymphoma kinase (ALK) and activated Cdc42-associated kinase (ACK1), the compound can have improved therapeutic effects against cancer cells having ALK fusion proteins such as EML4-ALK and NPM-ALK and is expected to be effective in preventing the recurrence of cancer. Therefore, the compound can be effectively used as a composition for preventing or treating cancer.

HETEROCYCLIC COMPOUNDS AND METHODS OF USE

Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

DERIVATIVES OF 1-PHENYL-1,5-DIHYDRO-BENZO[B] [1.4]DIAZEPINE-2.4-DIONE AS INHIBITORS OF HIV REPLICATION

Compounds of formula (I) wherein m, R1, R2, R3, X and Y are defined herein, are useful as inhibitors of HIV replication.

Methods of treating or preventing sleep apnea

This invention provides methods for the treatment or prevention of sleep apnea in a mammal which compris administering to a mammal in need thereof an effective amount of a substituted benzimidazole, or a pharmaceutically acceptable salt or solvate thereof.

Methods of treating or preventing interstitial cystitis

PCT No. PCT/US97/03895 Sec. 371 Date Aug. 25, 1998 Sec. 102(e) Date Aug. 25, 1998 PCT Filed Mar. 7, 1997 PCT Pub. No. WO97/33873 PCT Pub. Date Sep. 18, 1997This invention provides methods for the treatment or prevention of interstitial cystitis or urethral syndrome in a mammal which comprise administering to a mammal in need thereof an effective amount of a substituted benzimidazole, or a pharmaceutically acceptable salt or solvate thereof.

METHODS FOR TREATING A PHYSIOLOGICAL DISORDER ASSOCIATED WITH BETA-AMYLOID PEPTIDE

This invention provides substituted benzimidazoles which are useful in treating or preventing conditions associated with beta-amyloid peptide. Some such conditions associated with beta-amyloid peptide include Alzheimer's Disease, Down's Symdrome and amyloidosis of the Dutch type