5-Amino-2,4,6-triiodoisophthaloyl dichloride

Description5-Amino-2,4,6-triiodoisophthaloyl dichloride is a triiodinated compound that has been shown to bind to the receptor for asialoglycoprotein. It is used in the diagnosis of liver and kidney diseases. 5-Amino-2,4,6-triiodisophthaloyl acid dichloride is taken up by tissues and organs and causes damage to these tissues. The chloride ion binds to the molecule, making it more water soluble. The lactobionic acid residue is then cleaved off by an enzyme in the cell called beta-galactosidase. This leaves a molecule containing iodine which can be detected with a diagnostic technique such as X-ray crystallography or nuclear magnetic resonance spectroscopy.

Uses5-Amino-2,4,6- triiodisophthaloyl acid dichloride is used in the preparation of trimeric X-ray contrast agents.

Preparation5-Amino-2,4,6-triiodo-isophtalic acid (30 g, 0.054 mol), thionyl chloride (8.2 ml, 0.113 mol) and pyridine (0.2 ml) in 1 ,2 dichloroethane (20 ml) were heated to 70 ℃. A portion of thionyl chloride (15.2 ml, 0.21 mol) was added dropwise during 2 h, and the mixture was heated to 85 ℃ for 6 h. After cooling the reaction mixture to room temperature, it was poured into 300 g of ice-water. The yellow precipitate was filtered off, sucked dry and then washed with water until pH=5. The filter cake was then dried in a vacuum oven for 3 hrs. A light yellow powder was obtained as 5-Amino-2,4,6-triiodisophthaloyl acid dichloride.