Chlorfenapyr

Base Information

• Chemical Name: Chlorfenapyr
• CAS No.: 122453-73-0
• Molecular Formula: C15H11BrClF3N2O
• Molecular Weight: 407.617
• European Community (EC) Number: 602-782-4
• UNII: NWI20P05EB
• DSSTox Substance ID: DTXSID9032533
• Nikkaji Number: J582.370F
• Wikipedia: Chlorfenapyr
• Wikidata: Q426475
• Metabolomics Workbench ID: 56253
• ChEMBL ID: CHEMBL1869551
• Mol file: 122453-73-0.mol

Synonyms:AC 303630;AC303630;chlorfenapyr

Chemical Property of Chlorfenapyr

Chemical Property:

• Appearance/Colour: off-white to light brown powder with an halide odor
• Vapor Pressure: 4.6E-08mmHg at 25°C
• Melting Point: 100.5oC
• Refractive Index: 1.559
• Boiling Point: 443.5 °C at 760 mmHg
• PKA: -18.00±0.70(Predicted)
• Flash Point: 222 °C
• PSA: 37.95000
• Density: 1.53 g/cm³
• LogP: 5.45548
• Storage Temp.: 0-6°C
• Water Solubility.: Insoluble in water
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 405.96954
• Heavy Atom Count: 23
• Complexity: 448

Purity/Quality:

98%tc ^*data from raw suppliers

Chlorfenapyr ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T;N,N,T
• Statements: 22-23-50/53
• Safety Statements: 13-36/37-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: CCOCN1C(=C(C(=C1C(F)(F)F)Br)C#N)C2=CC=C(C=C2)Cl
• Description: Chlorfenapyr is a broad spectrum pesticide which is not approved for use in the EU, and only approved for limited applications in the US (applications for ornamental plants in greenhouses). It was originally rejected for FDA approval due to avian and aquatic toxicity. Data on human toxicity is still scarce, but it has moderate mammalian toxicity when taken orally, causing vacuolation of the nervous system in mice and rats. It is not persistent in ecosystems, and has low aqueous solubility. Chlorfenapyr can also be used as an insect-proofing agent in wool, and has been investigated for applications in malaria control. Chlorfenapyr is a pyrrole pro-insecticide that is metabolized in vivo into CL 303268 by mixed function oxidases. Chlorfenapyr increases respiratory activity in German cockroaches when used at concentrations ranging from 1 to 10 μg per insect but has no effect on respiration in Sf9 cells when used at concentrations ranging from 1 to 100 μM and does not affect respiration in isolated rat liver mitochondria up to a concentration of 10 μM. Chlorfenapyr is active against a variety of insects including those susceptible and resistant to pyrethroid and organophosphate insecticides, including horn flies (H. irritans) as well as A. culicifacies and A. stephensi mosquitos that carry malaria (LC50s = 2-2.39% suspension impregnated on paper). Chlorfenapyr is lethal to rats with LD50 values of 441 and 1,152 mg/kg for male and female rats, respectively. Formulations containing chlorfenapyr have been used to control termites and in agriculture to control various insects.
• Uses: Chlorfenapyr is a halogenated pyrrole based pro-insecticide. Chlorfenapyr functions by metabolizing into an active insecticide after entering the host. Chlorfenapyr is used primarily as a means of pes t control on cotton. Insecticide. Acaricide.

Technology Process of Chlorfenapyr

There total 8 articles about Chlorfenapyr which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

tralopyril (122454-29-9) + ethyl chloromethyl ether (3188-13-4) → chlorfenapyr (122453-73-0)

Guidance literature:

tralopyril; With sodium hydroxide; at 20 ℃; for 0.333333h;

ethyl chloromethyl ether; at 60 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 92.3%

formaldehyde diethyl acetal (462-95-3) + tralopyril (122454-29-9) → chlorfenapyr (122453-73-0)

Guidance literature:

formaldehyde diethyl acetal; tralopyril; With trichlorophosphate; In toluene; at 97 ℃; for 0.5h;

With triethylamine; In toluene; at 97 ℃; for 5h;

Reference yield:

4-bromo-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile → chlorfenapyr (122453-73-0)

Guidance literature:

With sodium ethanolate; In ethanol;

upstream raw materials:

tralopyril

ethyl chloromethyl ether

formaldehyde diethyl acetal

2-(4-Chlorophenyl)glycine

Refernces

• 1、 -. "Application of 2-aryl substituted pyrrole compound in medicine for killing oncomelania hupensis". Paragraph 0144; 0146; 0150; 0152. . Retrieved 2019/01/08.
• 2、 -. "NOVEL CRYSTALLINE FORM OF CHLORFENAPYR, PROCESS FOR ITS PREPARATION AND USE". Paragraph 0068; 0069. . Retrieved 2018/06/06.