Rafoxanide

Base Information

• Chemical Name: Rafoxanide
• CAS No.: 22662-39-1
• Molecular Formula: C19H11Cl2I2NO3
• Molecular Weight: 626.016
• Hs Code.: DERIVATION
• European Community (EC) Number: 245-148-9
• NSC Number: 355278
• UNII: 22F4FLA7DH
• DSSTox Substance ID: DTXSID5046227
• Nikkaji Number: J11.487A
• Wikipedia: Rafoxanide
• Wikidata: Q12048733
• NCI Thesaurus Code: C152146
• ChEMBL ID: CHEMBL287542
• Mol file: 22662-39-1.mol

Synonyms:Disalan;Flukanide;MK 990;Rafoxanid;Rafoxanide;Ranide

Chemical Property of Rafoxanide

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 1.05E-11mmHg at 25°C
• Melting Point: 169ºC
• Refractive Index: 1.752
• Boiling Point: 526.6 °C at 760 mmHg
• PKA: 6.04±0.48(Predicted)
• Flash Point: 272.3 °C
• PSA: 58.56000
• Density: 2.05 g/cm³
• LogP: 7.02580
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 624.82054
• Heavy Atom Count: 27
• Complexity: 507

Purity/Quality:

99% ^*data from raw suppliers

Rafoxanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1OC2=C(C=C(C=C2)NC(=O)C3=C(C(=CC(=C3)I)I)O)Cl)Cl
• Uses: Rafoxanide is a thyroid hormone receptor.

Technology Process of Rafoxanide

There total 5 articles about Rafoxanide 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: 92.1%

2-hydroxy-3,5-diiodobenzoic acid chloride + 4-amino-2-chlorophenyl-p-chlorophenyl ether → rafoxanide (22662-39-1)

Guidance literature:

at 20 - 40 ℃; for 1h;

Reference yield:

3-chloro-4-(4-chlorophenoxy)-benzenamine (24900-79-6) + 3,5-diiodosalicylic acid (133-91-5) → rafoxanide (22662-39-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/acs.orglett.8b03014

Reference yield:

3,4-dichloronitrobenzene (99-54-7) → rafoxanide (22662-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.33 h / 35 °C

1.2: 5 h / Reflux

2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 2 h / 55 °C / 150.01 Torr / Inert atmosphere

3.1: 1 h / 20 - 40 °C

With palladium 10% on activated carbon; hydrogen; potassium hydroxide; In ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

3,4-dichloronitrobenzene

3-chloro-4-(4-chlorophenoxy)-benzenamine

3,5-diiodosalicylic acid

Refernces

• 1、 Ni, Jizhi,Oguro, Tsubasa,Sawazaki, Taka,Sohma, Youhei,Kanai, Motomu. "Hydroxy Group Directed Catalytic Hydrosilylation of Amides". supporting information. p. 7371 - 7374. Retrieved 2018/11/25.
• 2、 -. "Compositions and methods for the treatment of helminthiasis". . . Retrieved 2008/06/13.