iotroxic acid

iotroxic acid Basic information
Product Name:iotroxic acid
Synonyms:iotroxic acid;Iotroxic;3,3'-[Oxybis[2,1-ethanediyloxy(1-oxo-2,1-ethanediyl)imino]]bis(2,4,6-triiodobenzoic acid);3,3'-[Oxybis[2,1-ethanediyloxy(1-oxo-2,1-ethanediyl)imino]]bis[2,4,6-triiodobenzoic acid];Biliscopin;SH-213AB;3-[[2-[2-[2-[2-(3-carboxy-2,4,6-triiodoanilino)-2-oxoethoxy]ethoxy]ethoxy]acetyl]amino]-2,4,6-triiodobenzoic acid;Benzoic acid, 3,3'-[oxybis[2,1-ethanediyloxy(1-oxo-2,1-ethanediyl)imino]]bis[2,4,6-triiodo-
CAS:51022-74-3
MF:C22H18I6N2O9
MW:1215.81
EINECS:256-917-3
Product Categories:
Mol File:51022-74-3.mol
iotroxic acid Structure
iotroxic acid Chemical Properties
density 2.4781 (estimate)
vapor pressure 0Pa at 25℃
Water Solubility 304mg/L at 20℃
LogP3.35 at 20℃
Safety Information
MSDS Information
iotroxic acid Usage And Synthesis
OriginatorBiliscopin,Schering,W. Germany,1978
UsesDiagnostic aid (radiopaque medium).
DefinitionChEBI: Iotroxic acid is an organic molecular entity.
Manufacturing Process(a) Condensation in dimethylacetamide: To a suspension of 51.5 g of anhydrous 3-amino-2,4,6-triiodo-benzoic acid (0.1 mol) in 100 ml of dimethylacetamide were slowly added dropwise, while stirring, 15.5 g of 3,6,9-trioxaundecanediacid dichloride (0.06 mol), during which the temperature gradually rose to about 50°C and the whole passed into solution. After being stirred overnight, the solution was added dropwise to 1 liter of a 0.28 N solution of sodium hydroxide, and then 200 ml of 2 N hydrochloric acid were cautiously added. The precipitate was filtered off with suction, washed with water and dried. The yield was practically quantitative.
(b) Condensation in dioxan: 15.5 g of 3,6,9-trioxaundecane diacid dichloride were added dropwise at about 95°C to a solution of 51.5 g of anhydrous 3- amino-2,4,6-triiodo-benzoic acid in 52 ml of anhydrous dioxan. After further stirring and heating for 3 hours, the solution was cooled, stirred dropwise into 500 ml of a 0.4 N solution of sodium hydroxide, and further worked up as described in paragraph (a). The yield was practically quantitative.
(c) Purification: To the crude product obtained as described under paragraph (a) or (b) in 300 ml of methanol was slowly added a quantity (about 15 ml) of a 12 N solution of sodium hydroxide such that a test portion diluted with water had a pH-value of 8 to 9. After stirring the mixture overnight, the sodium salt of 3,6,9-trioxaundecane-1,11-dioyl-bis-(3-carboxy-2,4,6-triodoanilide) which crystallized out was filtered off with suction, was hed with methanol and dried. Yield: 92 g (90% of the theoretical yield).
A solution of the salt in 900 ml of water was treated with active carbon, and concentrated hydrochloric acid was added until the pH-value was 1. The precipitate was filtered off with suction, washed with water, and dried at 50°C.
The yield of pure 3,6,9-trioxaundecane-1,11-dioyl-bis-(3-carboxy-2,4,6- triiodo-anilide) was 80 g (80% of the theoretical yield). The substance melted at 175°C with sintering.



Therapeutic FunctionDiagnostic aid (radiopaque medium)
Flammability and ExplosibilityNotclassified
iotroxic acid Preparation Products And Raw materials
Raw materials2,6-Dibromopyridin-3-amine-->3-Amino-2,4,6-triiodobenzoic acid
3,6,9-trioxaundecamethylenediamine iotroxic acid 4-Iodobenzoic acid 3-[(methoxyacetyl)amino]benzoic acid iotroxic acid meglumine salt

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