IOXITALAMIC ACID CAS 28179-44-4
Introduction：Basic information about IOXITALAMIC ACID CAS 28179-44-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
IOXITALAMIC ACID Basic information
| Product Name: | IOXITALAMIC ACID |
| Synonyms: | Ioxitalamic;Acidum Joxitalamicum;2,4,6-Triiodo-3-(acetylamino)-5-(2-hydroxyethylcarbamoyl)benzoic acid;3-(Acetylamino)-2,4,6-triiodo-5-[[(2-hydroxyethyl)amino]carbonyl]benzoic acid;IOXITALAMIC ACID;sodium 3-acetamido-5-[(2-hydroxyethylamino)-oxomethyl]-2,4,6-triiodobenzoate;3-(AcetylaMino)-5-[[(2-hydroxyethyl)aMino]carbonyl]-2,4,6-triiodobenzoic Acid;3-AcetaMido-2,4,6-triiodo-(N-β-hydroxyethyl)isophthalic Acid MonoaMide |
| CAS: | 28179-44-4 |
| MF: | C12H11I3N2O5 |
| MW: | 643.94 |
| EINECS: | 248-887-5 |
| Product Categories: | Amines;Aromatics;Diagnostic;Isotope Labelled Compounds;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 28179-44-4.mol |
IOXITALAMIC ACID Chemical Properties
| Melting point | 253-255?C |
| Boiling point | 582.8±50.0 °C(Predicted) |
| density | 2.519±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,2-8°C |
| solubility | DMSO (Slightly, Heated), Methanol (Slightly) |
| form | Solid |
| pka | 0.85±0.10(Predicted) |
| color | Off-White to Pale Brown |
| InChI | 1S/C12H11I3N2O5/c1-4(19)17-10-8(14)5(11(20)16-2-3-18)7(13)6(9(10)15)12(21)22/h18H,2-3H2,1H3,(H,16,20)(H,17,19)(H,21,22) |
| InChIKey | OLAOYPRJVHUHCF-UHFFFAOYSA-N |
| SMILES | IC1=C(NC(C)=O)C(I)=C(C(O)=O)C(I)=C1C(NCCO)=O |
Safety Information
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral |
| Chemical Properties | White Solid |
| Originator | Oxilan,Cook Imaging Corporation |
| Uses | A substituted 2,4,6-triiodobenzoic acid, an excellent contrast media for ventriculography, radiculography, lumbar myelography and x-rays of the cardiovascular system. |
| Definition | ChEBI: An organoiodine compound that is 2,4,6-triiodobenzoic acid substituted by an acetylamino group at position 3 and a (2-hydroxyethyl)carbamoyl group at position 5. It is used as a contrast medium. |
| Manufacturing Process | 3-Methoxycarboxyl-5-nitrobenzoic acid (25 g) was hydrogenated in methanol(500 ml) using palladium oxide on charcoal (2.5 g 10%) at atmosphericpressure. When the exothermic reaction was completed the catalyst wasfluttered off. After cooling the solution at -20°C for 2.5 h, 12.7 g of 3-amino-5-methoxycarbonylbenzoic acid was isolated. An additional 6.5 g of it wasisolated by concentrating the mother liquor. The 3-amino-5-methoxycarbonylbenzoic acid (12.0 g) was suspended in water(280 ml), dissolved by addition of concentrated hydrochloric acid (7.1 ml) andglacial acetic acid (28.5 ml). At 60°-70°C NaICl2 solution (73 ml, 58.7 gICl/100 ml) was added dropwise while stirring in the course of about 3 h. Thereaction mixture was heated at 80°-90°C for additional 3 h while stirring. After cooling to room temperature the mother liquor was decanted and theresidue dissolved as ammonium salt in water (80 ml). The ammonium saltwas precipitated by adding ammonium chloride (2.4 g) and cooling to 0°C.The ammonium salt was filtered off and dissolved in water (140 ml),charcoaled twice at 80°C and the acid was precipitated at room temperatureby addition of hydrochloric acid and was filtered off. The crude product wasdissolved in ethyl acetate (100 ml) and the solution was washed 3 times withhydrochloric acid (2 N). By evaporating the solvent, 19 g of 3-amino-5-methoxycarbonyl-2,4,6-triiodobenzoic acid was isolated. Melting point 170°-176°C. A mixture of 3-amino-5-methoxycarbonyl-2,4,6-triiodobenzoic acid (198 g)and thionyl chloride (400 ml) was heated while stirring at 70°C for 16 h. Thesolid material dissolved slowly. Thionyl chloride was evaporated in vacuo, theresidue dissolved in chloroform (1000 ml), the solution washed with water (80ml each), twice with saturated sodium bicarbonate, then 5 times with 2 Nsodium hydroxide solution and finally with water to neutral. The solution wasdried with CaCl2 filtered and evaporated to dryness. The 3-amino-5-methoxycarbonyl-2,4,6-triiodobenzoyl chloride was dried at 50°C in vacuo.Yield: 203.0 g. Melting point 55°-60°C. To the 3-amino-5-methoxycarbonyl-2,4,6-triiodobenzoyl chloride (53.0 g) wasadded acetic anhydride (106 ml). After stirring at room temperature for 20min then insoluble material was filtered off (3-4 g). To the filtrate was addedconcentrated sulfuric acid (0.3 ml) whereby a yellowish product started toprecipitate. The temperature reached about 50°C. The 3-acetamido-5-methoxycarbonyl-2,4,6-triiodobenzoyl chloride was isolated after storing inrefrigerator overnight. Yield: 39.0 g. Melting point 210°-215°C. The 3-acetamido-5-methoxycarbonyl-2,4,6-triiodobenzoyl chloride wasdissolved in a mixture of dioxan and dimethylformamide. In the course of 2 hthis solution was added dropwise to a solution of ethanolamine andtriethylamine in dioxan. The stirring was continued. A sticky precipitate wasfiltered off. The filtrate was evaporated to dryness in vacuo. The residue wastriturated with aqueous sodium bicarbonate, filtered off and mixed with firstfraction. The combined solids were then suspended in aqueous sodiumbicarbonate filtered off washed with water and dried in vacuo to give methyl5-acetamido-2,4,6-triiodo-(N-β-hydroxyethyl)-isophthalamate. The methyl 5-acetamido-2,4,6-triiodo-(N-β-hydroxyethyl)-isophthalamate wasmixed with fresh distilled ethanolamine and stirred. The excess ethanolaminewas removed in vacuo at 50°-60°C. The residue was dissolved in water, andcharcoaled at pH 5.5. The crude product was precipitated with hydrochloricacid (pH 0.5) and filtered after stirring at 0°C. 5-Acetamido-2,4,6-triiodo-(N-β-hydroxyethyl)isophthalamic acid was suspended in ethanol and dissolved byaddition of concentrated ammonia. The ammonium salt started to precipitatein the course and was isolated after stirring. The salt was dissolved in water,filtered and the acid was precipitated with hydrochloric acid (pH 0.5). Afterstirring the product was filtered off and dried in vacuo. |
| Therapeutic Function | Diagnostic aid |
IOXITALAMIC ACID Preparation Products And Raw materials
| Raw materials | Ammonia-->Sulfuric acid-->Thionyl chloride-->Sodium hydroxide-->Acetic acid-->Sodium bicarbonate-->Hydrochloric acid-->Ammonium chloride-->Triethylamine-->Acetic anhydride-->Monoethanolamine |
