Closantel

Base Information

• Chemical Name: Closantel
• CAS No.: 57808-65-8
• Molecular Formula: C22H14Cl2I2N2O2
• Molecular Weight: 663.08
• European Community (EC) Number: 260-967-1
• NSC Number: 759819,335306
• UNII: EUL532EI54
• DSSTox Substance ID: DTXSID6040662
• Nikkaji Number: J12.605E
• Wikidata: Q2560163
• NCI Thesaurus Code: C79920
• Pharos Ligand ID: SDZNMMPYWU9G
• ChEMBL ID: CHEMBL12131
• Mol file: 57808-65-8.mol

Synonyms:closantel;N-(5-chloro-4((4-chlorophenyl)cyanomethyl)-2-methylphenyl)-2-hydroxy-3,5-diiodobenzamide

Chemical Property of Closantel

Chemical Property:

• Appearance/Colour: white to yellowish powder
• Vapor Pressure: 1.53E-14mmHg at 25°C
• Melting Point: 210 - 22oC
• Refractive Index: 1.736
• Boiling Point: 590.5 °C at 760 mmHg
• PKA: 5.99±0.48(Predicted)
• Flash Point: 310.9 °C
• PSA: 73.12000
• Density: 1.943 g/cm³
• LogP: 7.19738
• Storage Temp.: 0-6°C
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 661.85218
• Heavy Atom Count: 30
• Complexity: 652

Purity/Quality:

99% ^*data from raw suppliers

Closantel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1NC(=O)C2=C(C(=CC(=C2)I)I)O)Cl)C(C#N)C3=CC=C(C=C3)Cl
• Description: Closantel is a kind of synthetic anti parasitic agent which is actively against liver fluke, bloodsucking nematodes and larval stages of some arthropods in sheep and cattle. Its mechanism of action is through decoupling the mitochondrial oxidative phosphorylation, thus inhibiting the production of ATP. Therefore, it inhibit their energy generation of the parasite, causing their death. It is mainly used for the treatment and prevention of several infections caused by many kinds of parasites such as Fasciola hepatica, Fasciola gigantica, Haemonchus concortus, Haemonchus placei, Bunostomum phlebotomum, Oesophagostomum radiatum and Strongyloides papillosus in cattle and sheep.
• Uses: antianginal, antihypertensive

Technology Process of Closantel

There total 6 articles about Closantel 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: 89.1%

2-(4-amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile (61437-85-2) → closantel (57808-65-8)

Guidance literature:

In toluene; at 50 ℃; for 6h; Solvent; Reflux; Sealed tube;

Reference yield:

1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + 2-hydroxy-3,5-diiodobenzoyl chloride (42016-91-1) + 2-(4-amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile (61437-85-2) → closantel (57808-65-8)

Guidance literature:

Reference yield:

p-chlorobenzyl cyanide (140-53-4) → closantel (57808-65-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate; methanol / 3 h / 50 °C / Sealed tube

2: hydrazine hydrate; sodium hydroxide / diethylene glycol / 6 h / 200 °C / Sealed tube

3: toluene / 6 h / 50 °C / Reflux; Sealed tube

With methanol; sodium methylate; hydrazine hydrate; sodium hydroxide; In toluene; diethylene glycol;

upstream raw materials:

1,4-dioxane

2-hydroxy-3,5-diiodobenzoyl chloride

2-(4-amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile

p-chlorobenzyl cyanide

Refernces

• 1、 -. "Antiparasitic salicylanilide derivatives". . . Retrieved 2008/06/13.