Iodixanol CAS 92339-11-2
Introduction：Basic information about Iodixanol CAS 92339-11-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Iodixanol Basic information
| Product Name: | Iodixanol |
| Synonyms: | Acupaque;DU-6807;5-[acetyl-[3-[N-acetyl-3,5-bis[(2,3-dihydroxypropylamino)-oxomethyl]-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide;Iodixanol (200 mg);5,5'-[(2-Hydroxy-1,3-propanediyl)bis(acetyliMino)]bis[N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-;odixanol;IODIXANOL;1,3-benzenedicarboxamide,5,5’-((2-hydroxy-1,3-propanediyl)bis(acetylimino))bis |
| CAS: | 92339-11-2 |
| MF: | C35H44I6N6O15 |
| MW: | 1550.18 |
| EINECS: | 618-837-0 |
| Product Categories: | Aromatics;Diagnostic;Intermediates & Fine Chemicals;Pharmaceuticals;92339-11-2 |
| Mol File: | 92339-11-2.mol |
Iodixanol Chemical Properties
| Melting point | 262-267°C (dec.) |
| Boiling point | 1250.9±65.0 °C(Predicted) |
| density | 1.266 ±0.003 |
| vapor pressure | 0Pa at 20℃ |
| refractive index | n 1.4128 ±0.0003 |
| storage temp. | Refrigerator |
| solubility | Freely soluble in water, sparingly soluble in methanol, practically insoluble in methylene chloride. |
| pka | 11.04±0.46(Predicted) |
| form | liquid |
| color | White |
| Major Application | pharmaceutical (small molecule) |
| InChIKey | NBQNWMBBSKPBAY-UHFFFAOYSA-N |
| SMILES | C(N(C1C(I)=C(C(NCC(O)CO)=O)C(I)=C(C(NCC(O)CO)=O)C=1I)C(C)=O)C(O)CN(C1C(I)=C(C(NCC(O)CO)=O)C(I)=C(C(NCC(O)CO)=O)C=1I)C(C)=O |
| LogP | 0.7 |
| EPA Substance Registry System | 1,3-Benzenedicarboxamide, 5,5'-[(2-hydroxy-1,3-propanediyl)bis(acetylimino)]bis[N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo- (92339-11-2) |
Safety Information
| WGK Germany | WGK 1 |
| HS Code | 2924296000 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 92339-11-2(Hazardous Substances Data) |
| Toxicity | LD50 i.v. in mice: 21 gI/kg (Palmers) |
| Chemical Properties | White Solid |
| Originator | OptiPrep,Nycomed Pharma,Norway |
| Uses | Nonionic, dimeric x-ray contrast medium. Diagnostic aid (radiopaque medium). |
| Definition | ChEBI: A dimeric, non-ionic, water-soluble, radiographic contrast agent, used particularly in coronary angiography. |
| Manufacturing Process | Dimethyl 5-nitroisophthalate (215 g) and 1-amino-2,3-propandiol (196 g)were refluxed in methanol (500 ml). After twenty hours the solution wascooled and stored in a refrigerator overnight. The product 5-nitro-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide was filtered and washed withmethanol. Yield: 270 g (84%). M.p. 128-132°C. 5-Nitro-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide (18.1 g) was suspendedin water (250 ml), conc. hydrochloric acid (4.2 ml) and 10% PdO/charcoal(0.5 g) were added, and the mixture hydrogenated in a Parr apparatus for oneday. After filtration the filtrate was heated at 80-90°C and 3.88 M NaICl2(42.5 ml) was added through a dropping funnel over 1 hour. The solution washeated for 2.5 hours. After cooling to 20°C 5-amino-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide crystallized out. 5-Amino-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide (110 g)was suspended in acetic anhydride (480 ml) and heated to 50°C.Concentrated sulfuric acid (3 ml) was then added. The starting material wasdissolved after a few minutes, and the reaction mixture was heated at 60°Cfor 75 min. After cooling the residue dissolved in methanol (300 ml) withwater (150 ml) the solution was heated to 50°C and the pH adjusted to about10.5 by 10 N sodium hydroxide. After 4-5 hours the pH didn't decrease, andthe hydrolysis was complete. The reaction mixture was cooled to 20°C andneutralized by adding hydrochloric acid. After stirring overnight 5-Acetamido-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide was filtered andwashed with water. Yield: 94 g (80%). Melting point 275°C, dec. 2-Methoxyethanol (300 ml) and sodium hydroxide (20 g) was added to thereactor at 50°C, and 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophtalamide (304 g) was added after two hours of stirring. All solidswere allowed to dissolve overnight before cooling to 30°C and adjustment topH 12 with diluted hydrochloric acid. Epichlorohydrin (11 g) was added to thesolution after further cooling to 15°C, and the reaction was allowed to proceedfor 51 hours. As a result 1,3-bis(acetamido)-N,N'-bis[3,5-bis(2,3-dihydroxypropylaminocarbonyl)-2,4,6-triiodophenyl]-2-hydroxypropane wasobtained. |
| Brand name | Visipaque (GE Healthcare). |
| Therapeutic Function | Diagnostic aid |
| General Description | Iodixanol is a viscous, isosmolar,nonionic, water-soluble dimer with 49% iodine content.It is formulated as an isotonic solution for intravascular injectionand indicated for excretory urography, angiography,and CT procedures. |
Iodixanol Preparation Products And Raw materials
| Raw materials | 1,3-Dichloro-2-propanol-->Sulfuric acid-->Dimethyl 5-nitroisophthalate-->Epichlorohydrin-->Sodium hydroxide-->Hydrochloric acid-->2-Methoxyethanol-->Acetic anhydride |
