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118353-04-1

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118353-04-1 Usage

General Description

4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline is a chemical compound with the molecular formula C12H6Cl3N3O4. It is a synthetic pesticide and herbicide that is commonly used in the agricultural industry to control weeds and pests. The presence of chloro and nitro groups in the molecule gives it its herbicidal and pesticidal properties. It is also known to be a mutagen and a potential carcinogen, posing health risks to humans and the environment. Due to its potential toxicity, the use and application of 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline are tightly regulated in many countries.

Check Digit Verification of cas no

The CAS Registry Mumber 118353-04-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,3,5 and 3 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 118353-04:
(8*1)+(7*1)+(6*8)+(5*3)+(4*5)+(3*3)+(2*0)+(1*4)=111
111 % 10 = 1
So 118353-04-1 is a valid CAS Registry Number.
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

118353-04-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

1.2 Other means of identification

Product number -
Other names BEN640

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:118353-04-1 SDS

118353-04-1Synthetic route

2,3-dichlorophenol
576-24-9

2,3-dichlorophenol

4,5-dichloro-2-nitroaniline
6641-64-1

4,5-dichloro-2-nitroaniline

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at 125℃; for 3h;70%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

3-N-(methanesulfonyl)-5-chloro-6-(2,3dichlorophenoxy)-benzotriazole
139368-74-4

3-N-(methanesulfonyl)-5-chloro-6-(2,3dichlorophenoxy)-benzotriazole

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
With triethylamine In N-methyl-acetamide; water
2,3-dichlorophenol
576-24-9

2,3-dichlorophenol

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
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

N-(4,5-dichloro-2-nitrophenyl)acetamide

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
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-nitrophenyl acetamide

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 50℃; for 4h; Industry scale;
2,3-dichlorophenol
576-24-9

2,3-dichlorophenol

N-(4,5-dichloro-2-nitrophenyl)acetamide
5462-30-6

N-(4,5-dichloro-2-nitrophenyl)acetamide

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
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

carbon disulfide

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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione
68828-69-3

5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione

Conditions
ConditionsYield
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)-2-nitroaniline

4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine
139369-42-9

4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine

Conditions
ConditionsYield
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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

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

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole

Conditions
ConditionsYield
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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol
68828-69-3

6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol

Conditions
ConditionsYield
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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole hydrochloride
1378851-20-7

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole hydrochloride

Conditions
ConditionsYield
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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole methylsulfate
1380167-24-7

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole methylsulfate

Conditions
ConditionsYield
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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

triclabendazole methanesulfonate

triclabendazole methanesulfonate

Conditions
ConditionsYield
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

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

triclabendazole
68786-66-3

triclabendazole

Conditions
ConditionsYield
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

118353-04-1Relevant articles and documents

PROCESS FOR PREPARATION OF TRICLABENDAZOLE

-

Paragraph 0024, (2013/11/19)

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.

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

Hernández-Luis, Francisco,Hernández-Campos, Alicia,Castillo, Rafael,Navarrete-Vázquez, Gabriel,Soria-Arteche, Olivia,Hernández-Hernández, Manuel,Yépez-Mulia, Lilián

experimental part, p. 3135 - 3141 (2010/09/03)

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.

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