22544-04-3

Basic information

• Product Name: 2-CHLORO-1-(2,4-DICHLOROPHENOXY)-4-NITROBENZENE
• Synonyms: 2-CHLORO-1-(2,4-DICHLOROPHENOXY)-4-NITROBENZENE;3-CHLORO-4-(2,4-DICHLOROPHENOXY)NITROBENZENE;2-Chloro-1-(2,4-dichlorophenoxy)-4-nitrobenzene, 95%+%
• CAS NO: 22544-04-3
• Molecular Formula: C₁₂H₆Cl₃NO₃
• Molecular Weight: 318.54
• Mol File: 22544-04-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 70-72°C
• Boiling Point: 360.6°Cat760mmHg
• Flash Point: 171.9°C
• Appearance: /
• Density: 1.451g/cm³
• Vapor Pressure: 3.94E-05mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 2-CHLORO-1-(2,4-DICHLOROPHENOXY)-4-NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1-(2,4-DICHLOROPHENOXY)-4-NITROBENZENE(22544-04-3)
• EPA Substance Registry System: 2-CHLORO-1-(2,4-DICHLOROPHENOXY)-4-NITROBENZENE(22544-04-3)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-36/37
• Hazardous Substances Data: 22544-04-3(Hazardous Substances Data)

Usage

General Description

2-CHLORO-1-(2,4-DICHLOROPHENOXY)-4-NITROBENZENE, also known as Chlorpropham, is a synthetic chemical compound used mainly as a herbicide and plant growth regulator. It is a nitrobenzene compound, with two chlorine atoms and a phenoxy group attached to the benzene ring. Chlorpropham has been used to control the growth of weeds in various crops and is also used to inhibit sprouting in stored potatoes. It is considered to have low acute toxicity to both humans and the environment, but it has been classified as a possible human carcinogen and may have adverse effects on the reproductive system. Due to these concerns, its use is regulated in many countries.

InChI:InChI=1/C12H6Cl3NO3/c13-7-1-3-11(9(14)5-7)19-12-4-2-8(16(17)18)6-10(12)15/h1-6H

Upstream product

• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 120-83-2 2,4-dichlorophenol 
• 99-54-7 3,4-dichloronitrobenzene 

Downstream Products

• 56966-58-6 3-chloro-4-(2′,4′-dichlorophenoxy)aniline 

Relevant articles and documents

Structural Development of Salicylanilide-Based SPAK Inhibitors as Candidate Antihypertensive Agents

Hypertension is an important target for drug discovery. We have focused on the with-no-lysine kinase (WNK)-oxidative stress-responsive 1 (OSR1) and STE20/SPS1-related proline-alanine-rich protein kinase (SPAK)-NaCl cotransporter (NCC) signal cascade as a potential target, and we previously developed a screening system for inhibitors of WNK-OSR1/SPAK-NCC signaling. Herein we used this system to examine the structure-activity relationship (SAR) of salicylanilide derivatives as SPAK kinase inhibitors. Structural design and development based on our previous hit compound, aryloxybenzanilide derivative 2, and the veterinary anthelmintic closantel (3) led to the discovery of compound 10 a as a potent SPAK inhibitor with reduced toxicity. Compound 10 a decreased the phosphorylation level of NCC in mouse kidney in vivo, and appears to be a promising lead compound for a new class of antihypertensive drugs.

Natural Product Neopeltolide as a Cytochrome bc1 Complex Inhibitor: Mechanism of Action and Structural Modification

The marine natural product neopeltolide was isolated from a deep-water sponge specimen of the family Neopeltidae. Neopeltolide has been proven to be a new type of inhibitor of the cytochrome bc1 complex in the mitochondrial respiration chain. However, its detailed inhibition mechanism has remained unknown. In addition, neopeltolide is difficult to synthesize because of its very complex chemical structure. In the present work, the binding mode of neopeltolide was determined for the first time by integrating molecular docking, molecular dynamics simulations, and molecular mechanics Poisson-Boltzmann surface area calculations, which showed that neopeltolide is a Qo site inhibitor of the bc1 complex. Then, according to guidance via inhibitor-protein interaction analysis, structural modification was carried out with the aim to simplify the chemical structure of neopeltolide, leading to the synthesis of a series of new neopeltolide derivatives with much simpler chemical structures. The calculated binding energies (ΔGcal) of the newly synthesized analogues correlated very well (R2 = 0.90) with their experimental binding free energies (ΔGexp), which confirmed that the computational protocol was reliable. Compound 45, bearing a diphenyl ether fragment, was successfully designed and synthesized as the most potent candidate (IC50 = 12 nM) against porcine succinate cytochrome c reductase. The molecular modeling results indicate that compound 45 formed a π-π interaction with Phe274 and two hydrogen bonds with Glu271 and His161. The present work provides a new starting point for future fungicide discovery to overcome the resistance that the existing bc1 complex inhibitors are facing.

Control of parasites in animals by N-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and N-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives

Methods for treating an animal for endo and/or ecto parasite infestation and/or for protecting an animal from endo and/or ecto parasite infestation using N-phenyl-1,1,1-trifluoromethanesulfonamide compounds are provided, together with methods of making th