68-90-6

Basic information

• Product Name: BENZIODARONE
• Synonyms: BENZIODARONE;2329labaz;2-ethyl-3-(3’,5’-diiodo-4’-hydroxybenzoyl)-cumarone;3-(3,5-diiodo-4-hydroxybenzoyl)-2-ethyl-benzofura;3,5-diiodo-4-hydroxyphenyl2-ethyl-3-benzofuranylketone;aethyl-2-(3’,5’-dijod-4’-oxybenzoyl)-3cumaron;algocor;amplivix
• CAS NO: 68-90-6
• Molecular Formula: C₁₇H₁₂I₂O₃
• Molecular Weight: 518.08
• EINECS: 200-695-2
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 68-90-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 167°
• Boiling Point: 518.2°C at 760 mmHg
• Flash Point: 267.2°C
• Appearance: /
• Density: 1.9173 (estimate)
• Vapor Pressure: 2.35E-11mmHg at 25°C
• Refractive Index: 1.727
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: 5.881mg/L(20 oC)
• CAS DataBase Reference: BENZIODARONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZIODARONE(68-90-6)
• EPA Substance Registry System: BENZIODARONE(68-90-6)

Safety Data

• Hazardous Substances Data: 68-90-6(Hazardous Substances Data)

Usage

Originator

Amplivix,Sigma-Tau

Uses

Benziodarone is a uricosuric drug,it is used to effectively to control hyperuricemia in renal transplantation.

Manufacturing Process

The starting product 2-ethyl-3-benzofuranyl p-hydroxyphenyl ketone (benzaron) was prepared in 4 steps: 1. First step was a reaction of salicylic aldehyde with chloroacetone to produce 2-acetyl-1-benzofuran. 2. It was reduced by hydrazine hydrate in an alkaline medium by process of Hyuang-Minlon, J.A.C.S., 1946, 68, 2487 to give 2-ethyl-1-benzofurane. 3. 2-Ethyl-3-(4-methoxybenzoyl)-1-benzofuran was obtained from 2-ethyl-1- benzofuran and 4-methoxy-benzoylchloride in a presence of tin tetrachloride. 4. It was heated with pyridine hydrochloride at 200°-220°C to give 2-ethyl-3- benzofuranyl p-hydroxyphenyl ketone (benzaron) as described in N.P.B.Hoi, C.Beaudet; US Patent No. 3,012,042; Dec. 5, 1961. Benzaron (1 part) was dissolved in a very slight excess of 3% caustic soda. To this solution is gradually added a slight excess of iodine dissolved in a 25% aqueous solution of potassium iodide. The resultant solution is acidified with a 20% solution of sodium bisulphite, centrifuged, washed with water and then recrystallized in acetic acid to give of 2-ethyl-3-benzofuranyl 4-hydroxy-3,5- diiodophenyl ketone. MP: 167°C.

Therapeutic Function

Coronary vasodilator, Uricosuric

Safety Profile

A poison bj7 intraperitoneal and intravenous routes. Moderately toxic by ingestion. A flammable liquid. When heated to decomposition it emits toxic vapors of I-.

InChI:InChI=1/C17H12I2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3

Upstream product

• 3131-63-3 2-ethylbenzofuran 
• 90-02-8 salicylaldehyde 
• 1477-19-6 benzarone 
• 3343-80-4 (2-ethylbenzofuran-3-yl)(4-methoxyphenyl)methanone 

Relevant articles and documents

Compound for treatment or prevention of hyperuricemia or gout

The invention discloses a compound for treatment or prevention of hyperuricemia or gout. The compound is the compound shown as formula (I) or formula (II) or pharmaceutical acceptable salts thereof. The compound or its pharmaceutical acceptable salts can be applied to urate excretion promotion so as to treat or prevent hyperuricemia or gout. (formula (1), formula (II)).

Pharmaceutical compositions and methods of producing coronary vasodilation

Pharmaceutical compositions and methods of producing coronary vasodilation by administering substituted benzofurans, for example 2-n-butyl-3-[4' -(2-hydroxy-3-isopropylamino)propoxybenzoyl] benzofuran.