Deiodoamiodarone

Base Information

• Chemical Name: Deiodoamiodarone
• CAS No.: 23551-25-9
• Molecular Formula: C₂₅H₃₁NO₃
• Molecular Weight: 393.526
• UNII: 3ANM294M1O
• DSSTox Substance ID: DTXSID20178139
• Nikkaji Number: J385.167B
• Wikidata: Q27256973
• ChEMBL ID: CHEMBL461546
• Mol file: 23551-25-9.mol

Synonyms:Deiodoamiodarone;23551-25-9;Dideiodo Amiodarone;(2-butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)phenyl)methanone;(2-Butylbenzofuran-3-yl)(4-(2-(diethylamino)-ethoxy)phenyl)methanone;UNII-3ANM294M1O;3ANM294M1O;CHEMBL461546;2-Butyl-3-benzofuranyl p-[2-(diethylamino)ethoxy]phenylketone;Amiodarone hydrochloride impurity A [EP];Ketone, 2-butyl-3-benzofuranyl p-(2-(diethylamino)ethoxy)phenyl;Methanone, (2-butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)phenyl)-;Desdiiodoamiodarone;Bisdesiodoamiodarone;L 3937;SCHEMBL8509096;BDBM18961;2-Butyl-3-(4-.beta.-diethylaminoethoxybenzoyl)benzofuran;DTXSID20178139;Amiodarone hydrochloride impurity A;(2-Butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]phenyl]methanone;Bis Des-iodo amiodarone Hydrochloride;(2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]phenyl]methanone;FT-0666664;J-015147;Q27256973;AMIODARONE HYDROCHLORIDE IMPURITY A [EP IMPURITY];(2-{4-[(2-butyl-1-benzofuran-3-yl)carbonyl]phenoxy}ethyl)diethylamine;(2-Butyl-1-benzofuran-3-yl)(4-[2-(diethylamino)ethoxy]phenyl)methanone #;(2-butylbenzofuran-3-yl)[4-[2-(diethylamino)ethoxy]phenyl] methanone

Chemical Property of Deiodoamiodarone

Chemical Property:

• Boiling Point: 535.0±50.0 °C(Predicted)
• PKA: 9.47±0.25(Predicted)
• PSA: 42.68000
• Density: 1.080±0.06 g/cm3(Predicted)
• LogP: 5.72700
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 393.23039385
• Heavy Atom Count: 29
• Complexity: 485

Purity/Quality:

> 95% ^*data from raw suppliers

Dideiodo amiodarone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC=C(C=C3)OCCN(CC)CC
• Uses: Dideiodo Amiodarone (Amiodarone EP Impurity A) is an intermediate of Amiodarone (A632950).

Technology Process of Deiodoamiodarone

There total 2 articles about Deiodoamiodarone 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: 88.0%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → Dideiodoamiodarone (23551-25-9)

Guidance literature:

With potassium carbonate; sodium iodide; In water; toluene; at 20 ℃;

DOI:10.1016/j.bmcl.2008.08.013

Reference yield:

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) + 2-(diethylamino)ethyl chloride (100-35-6) → Dideiodoamiodarone (23551-25-9)

Guidance literature:

With sodium ethanolate;

DOI:10.1007/s002280050701

upstream raw materials:

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran

2-(diethylamino)ethyl chloride

2-chloro-N,N-diethylethylamine hydrochloride

Refernces

• 1、 Ha,Stieger,Grassi,Altorfer,Follath. "Structure effect relationships of amiodarone analogues on the inhibition of thyroxine deiodination". . p. 807 - 814. Retrieved 2007/10/03.