118353-04-1

Basic information

• Product Name: 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline
• Synonyms: 4-CHLORO-5-(2,3-DICHLOROPHENOXY)-2-NITROANILINE;5-AMINO-2'',2,3-TRICHLORO-4''-NITRODIPHENYL ETHER;4-CHLORO-5-(2,3-DICHLOROPHENOXY)-2-NITROANILINE,99%;Benzenamine, 4-chloro-5-(2,3-dichlorophenoxy)-2-nitro;4-(2,3-Dichlorophenoxy)-5-chloro-2-nitrobenzenamine;4-Chloro-5-(2,3-Dichloro phenoxy)-2-Nitro Aniline (TCPNA)
• CAS NO: 118353-04-1
• Molecular Formula: C₁₂H₇Cl₃N₂O₃
• Molecular Weight: 333.55
• Product Categories: API intermediates
• Mol File: 118353-04-1.mol

Chemical Properties

• Melting Point: 149-150 °C(Solv: benzene (71-43-2); ethanol (64-17-5))
• Boiling Point: 417.123 °C at 760 mmHg
• Flash Point: 206.069 °C
• Appearance: /
• Density: 1.588 g/cm³
• Vapor Pressure: 3.63E-07mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: 2-8°C
• PKA: -1.94±0.25(Predicted)
• CAS DataBase Reference: 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline(118353-04-1)
• EPA Substance Registry System: 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline(118353-04-1)

Safety Data

• Hazardous Substances Data: 118353-04-1(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline is used as a synthetic pesticide and herbicide for controlling weeds and pests in various crops. Its chloro and nitro groups provide the necessary herbicidal and pesticidal properties, making it an effective solution for agricultural needs.
However, due to its potential toxicity, mutagenicity, and carcinogenicity, the use of 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline is tightly regulated in many countries to minimize health risks to humans and the environment. It is essential to follow proper guidelines and regulations when using this compound in agricultural applications to ensure safety and sustainability.

InChI:InChI=1/C12H7Cl3N2O3/c13-6-2-1-3-10(12(6)15)20-11-5-8(16)9(17(18)19)4-7(11)14/h1-5H,16H2

Synthetic route

2,3-dichlorophenol (576-24-9) + 4,5-dichloro-2-nitroaniline (6641-64-1) → 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 125℃; for 3h;	70%

1,2,3-Benzotriazole (95-14-7) + 3-N-(methanesulfonyl)-5-chloro-6-(2,3dichlorophenoxy)-benzotriazole (139368-74-4) + methanesulfonyl chloride (124-63-0) → 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1)

Conditions	Yield
With triethylamine In N-methyl-acetamide; water

2,3-dichlorophenol (576-24-9) → 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Industry scale 2: sodium hydroxide; water / methanol / 4 h / 50 °C / Industry scale View Scheme

N-(4,5-dichloro-2-nitrophenyl)acetamide (5462-30-6) → 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Industry scale 2: sodium hydroxide; water / methanol / 4 h / 50 °C / Industry scale View Scheme

4-chloro-5-(2,3-dichlorophenoxy)-2-nitrophenyl acetamide → 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1)

Conditions	Yield
With water; sodium hydroxide In methanol at 50℃; for 4h; Industry scale;

2,3-dichlorophenol (576-24-9) + N-(4,5-dichloro-2-nitrophenyl)acetamide (5462-30-6) → 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1)

Conditions	Yield
Stage #1: 2,3-dichlorophenol; N-(4,5-dichloro-2-nitrophenyl)acetamide With potassium carbonate In N,N-dimethyl-formamide at 20 - 90℃; for 12h; Large scale; Stage #2: With sodium hydroxide In methanol; water; N,N-dimethyl-formamide at 50℃; for 4h; Large scale;	2 kg

carbon disulfide (75-15-0) + 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione (68828-69-3)

Conditions	Yield
Stage #1: 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline With trichlorosilane; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; Stage #2: carbon disulfide With potassium hydroxide In ethanol at 85℃; for 15.5h;	72%

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine (139369-42-9)

Conditions	Yield
With hydrogen In ethanol at 25℃;
With hydrogen; sodium hydroxide; Raney nickel In methanol at 100℃; for 12h; Industry scale;
With hydrogen; sodium hydroxide In methanol at 100℃; for 12h; Inert atmosphere;	810 g

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole (68786-66-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen; sodium hydroxide / Raney nickel / methanol / 12 h / 100 °C / Industry scale 2.1: sodium hydroxide / methanol / 6 h / Reflux; Industry scale 2.2: 4 h / 60 - 90 °C / Industry scale 3.1: sodium carbonate / water; methanol / 2 h / 60 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogen; sodium hydroxide / Raney nickel / methanol / 12 h / 100 °C / Industry scale 2.1: sodium hydroxide / methanol / 6 h / Reflux; Industry scale 2.2: 4 h / 60 - 90 °C / Industry scale 3.1: methanol / 6 h / 40 - 65 °C / Industry scale 4.1: hydrogenchloride / water; methanol / 1 h / 20 °C 5.1: ammonia / water View Scheme

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol (68828-69-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen; sodium hydroxide / Raney nickel / methanol / 12 h / 100 °C / Industry scale 2.1: sodium hydroxide / methanol / 6 h / Reflux; Industry scale 2.2: 4 h / 60 - 90 °C / Industry scale View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; hydrogen / methanol / 12 h / 100 °C / Inert atmosphere 2.1: methanol / 6 h / Reflux 2.2: 4 h / 60 - 90 °C View Scheme

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole hydrochloride (1378851-20-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogen; sodium hydroxide / Raney nickel / methanol / 12 h / 100 °C / Industry scale 2.1: sodium hydroxide / methanol / 6 h / Reflux; Industry scale 2.2: 4 h / 60 - 90 °C / Industry scale 3.1: methanol / 6 h / 40 - 65 °C / Industry scale 4.1: hydrogenchloride / water; methanol / 1 h / 20 °C View Scheme

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole methylsulfate (1380167-24-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen; sodium hydroxide / Raney nickel / methanol / 12 h / 100 °C / Industry scale 2.1: sodium hydroxide / methanol / 6 h / Reflux; Industry scale 2.2: 4 h / 60 - 90 °C / Industry scale 3.1: methanol / 6 h / 40 - 65 °C / Industry scale View Scheme

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → triclabendazole methanesulfonate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; hydrogen / methanol / 12 h / 100 °C / Inert atmosphere 2.1: methanol / 6 h / Reflux 2.2: 4 h / 60 - 90 °C 3.1: methanol / 6 h / 40 - 65 °C / Large scale View Scheme

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → triclabendazole (68786-66-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; hydrogen / methanol / 12 h / 100 °C / Inert atmosphere 2.1: methanol / 6 h / Reflux 2.2: 4 h / 60 - 90 °C 3.1: methanol; water / 0.5 h / 60 °C 3.2: 1.5 h / 60 °C View Scheme

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 139368-74-4 3-N-(methanesulfonyl)-5-chloro-6-(2,3dichlorophenoxy)-benzotriazole 
• 124-63-0 methanesulfonyl chloride 
• 576-24-9 2,3-dichlorophenol 
• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 5462-30-6 N-(4,5-dichloro-2-nitrophenyl)acetamide 

Downstream Products

• 139369-42-9 4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine 
• 68786-66-3 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole 
• 68828-69-3 6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol 
• 1378851-20-7 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole hydrochloride 
• 1380167-24-7 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole methylsulfate 
• 68786-66-3 triclabendazole 
• 68828-69-3 5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione 

Relevant articles and documents

PROCESS FOR PREPARATION OF TRICLABENDAZOLE

The present invention discloses a method for preparing Triclabendazole comprising condensing N-(4,5-dichloro-2-ni-trophenyl)acetamide with 2,3-dichlorophenol to obtain 4-chloro-5(2,3-dichlorophenoxy)-2-nitrophenyl acetamide and it to obtain 4-chloro-5(2,3-dichlorophenoxy)-2-nitroaniline; reducing 4-chloro-5(2,3-dichlorophenoxy)-2-nitroaniline in presence of Raney nickel to obtain 4-chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine of; cyclising 4-chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine in presence of carbondisulfide to obtain 6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol; methylating 6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol using a methylating agent to obtain triclabendazole methanesulfonate salt; converting triclabendazole methanesulfonate salt to hydrochloride salt of Triclabendazole and hydrolysing it to obtain Triclabendazole.

PROCESS FOR PREPARATION OF TRICLABENDAZOLE

The present invention discloses a method for preparing Triclabendazole comprising condensing N-(4,5-dichloro-2-nitrophenyl)acetamide with 2,3-dichlorophenol to obtain 4-chloro-5(2,3-dichlorophenoxy)-2-nitrophenyl acetamide and it to obtain 4- chloro-5(2,3-dichlorophenoxy)-2-nitroaniline; reducing 4-chloro-5(2,3- dichlorophenoxy)-2-nitroaniline in presence of Raney nickel to obtain 4-chloro-5- (2,3-dichlorophenoxy)benzene-l,2-diamine of; cyclising 4-chloro-5-(2,3- dichlorophenoxy)benzene-l,2-diamine in presence of carbondisulfide to obtain 6- chloro-5-(2,3-dichlorophenoxy)-lH-benzimidazole-2-thiol; methylating 6-chloro-5- (2,3-dichlorophenoxy)-lH-benzimidazole-2 -thiol using a methylating agent to obtain triclabendazole methanesulfonate salt; converting triclabendazole methanesulfonate salt to hydrochloride salt of Triclabendazole and hydrolysing it to obtain Triclabendazole.

Synthesis and biological activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives against some protozoa and Trichinella spiralis

A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives (1ae1i) were synthesized via Phillips cyclocondensation of a substituted 1,2-phenylenediamine and trifluoroacetic acid. The synthesized compounds were evaluated in vitro against various protozoan parasites: Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis and Leishmania mexicana, and they showed nanomolar activities against the first three protozoa tested. The compounds were also tested in vitro and in vivo against the nematode Trichinella spiralis. Compounds 1b, 1c and 1e had the most desirable in vitro antiparasitic profile against all parasites studied. In the in vivo model against T. spiralis, compounds 1b and 1e showed good activity against the adult phase at 75 mg/Kg. However, against the muscle larvae stage, only compound 1f exhibited in vivo antiparasitic efficacy.

Microbicidal benzotriazole compounds

Novel benzotriazolesulfonic acid derivatives of formula STR1 wherein: R1 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy having at least two identical or different halogen atoms, CF3, nitro or the group N(R')R", wherein R' and R" are each independently of the other C1 -C4 alkyl; R2 is phenoxy or phenylthio each of which is unsubstituted or mono- to tri-substituted by halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy having at least two identical or different halogen atoms, cyano, nitro, C2 -C4 alkenyl, C2 -C4 alkynyl, phenyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by halogen, C1 -C4 alkyl and/or by C1 -C4 alkoxy; or R2 is the radical O--CH2 --O; R3 is alkyl, aryl or aralkyl having a maximum of 14 carbon atoms, these radicals can be substituted by halogen, C1 -C4 alkyl and/or by nitro; including the position isomers of R1 and R2, insofar as those substituents occupy positions 5 and 6. The novel compounds have plant-protecting properties and are suitable especially for protecting plants against attack by phytopathogenic microorganisms such as fungi, especially Oomycetes.