DIATRIZOIC ACID

DIATRIZOIC ACID Basic information
Product Name:DIATRIZOIC ACID
Synonyms:2,4,6-triiodo-3,5-diacetamidobenzoicacid;3,5-bis(acetylamino)-2,4,6-triiodo-benzoicaci;3,5-diacetamido-2,4,6-triiodo-benzoicaci;amidotrizoate;diat;diatriazoate;3,5-BIS(ACETYLAMINO)-2,4,6-TRIIODOBENZOIC ACID;AMIDOTRIZOIC ACID
CAS:117-96-4
MF:C11H9I3N2O4
MW:613.91
EINECS:204-223-6
Product Categories:UROVIST;Intermediates & Fine Chemicals;Pharmaceuticals;Organics
Mol File:117-96-4.mol
DIATRIZOIC ACID Structure
DIATRIZOIC ACID Chemical Properties
Melting point >300°C
Boiling point 614.1±55.0 °C(Predicted)
density 2.4079 (estimate)
vapor pressure 0Pa at 20℃
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Soluble in Methanol.
form neat
pka0.92±0.10(Predicted)
color White to Off-White
Water Solubility 500g/L(25 ºC)
Merck 14,2992
Stability:Light Sensitive
InChIInChI=1S/C11H9I3N2O4/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18/h1-2H3,(H,15,17)(H,16,18)(H,19,20)
InChIKeyYVPYQUNUQOZFHG-UHFFFAOYSA-N
SMILESC(O)(=O)C1=C(I)C(NC(C)=O)=C(I)C(NC(C)=O)=C1I
LogP3.3 at 20℃
EPA Substance Registry SystemBenzoic acid, 3,5-bis(acetylamino)-2,4,6-triiodo- (117-96-4)
Safety Information
WGK Germany 3
RTECS DG5950000
HS Code 2924.29.7790
Hazardous Substances Data117-96-4(Hazardous Substances Data)
ToxicityLD50 intravenous in mouse: 8900mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
DIATRIZOIC ACID Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorHypaque Sodium,Winthrop,US,1955
Usesradiopaque agent
UsesDensity gradient reagent for blood cell seperation. Diagnostic aid (radiopaque medium)
UsesDiatrizoic acid is a gradient reagent used for blood cell separation and diagnostic aid (radiopaque medium). Diatrizoic acid may be used as an alternative to barium sulfate for medical imaging of the gastrointestinal tract, such as upper gastrointestinal series and small bowel series.
DefinitionChEBI: A member of the class of benzoic acids that is benzoic acid having iodo substituents at the 2-, 4- and 6-positions and acetamido substituents at the 3- and 5-positions. It is used, mainly as its N-methylglucamine and sodium salts, as an -ray contrast medium in gastrointestinal studies, angiography, and urography.
Manufacturing Process3,5-Dinitrobenzoic acid (15.9 g) was dissolved in an equivalent amount of sodium hydroxide solution, and the solution was diluted to 310 ml with water. The solution was refluxed with Raney nickel for fifteen minutes, filtered, and the filtrate was hydrogenated at elevated pressure using platinum oxide catalyst. After the amount of hydrogen calculated to reduce both nitro groups had been absorbed, the mixture was filtered, and the filtrate was acidified with an equal volume of concentrated hydrochloric acid. Iodine monochloride (17 ml) in 100 ml of 6N HCl was then added with stirring. The reaction mixture was allowed to stand for two and one-half hours at room temperature, then diluted with an equal amount of water with vigorous stirring, and the solid material was collected by filtration and recrystallized
from dilute methanol, giving 18.5 g of 3,5-diamino-2,4,6-triiodobenzoic acid, MP about 135°C with decomposition. The 18.5 g of 3,5-diamino-2,4,6- triiodobenzoic acid was suspended in 150 ml of acetic anhydride containing 5 drops of 70% perchloric acid, and the mixture was heated on a steam bath for three and one-half hours. The reaction mixture was poured into 300 ml of ice water, and then heated on a steam bath until crystallization took place. The solid material was collected by filtration, dissolvedin dilute sodium hydroxide solution, filtered, and hydrochloric acid was added to the filtrate to reprecipitate the acid product. The latter was again dissolved in sodium hydroxide and reprecipitated with acid, giving 9 g of 3,5-diacetamido-2,4,6- triiodobenzoic acid, MP above 250°C.
The acid may be used as the sodium salt or as the meglumate.

Brand nameMd (Mallinckrodt); Urovist Sodium (Berlex).
Therapeutic FunctionDiagnostic aid (radiopaque medium)
General DescriptionDiatrizoate is a water-soluble, ionicmonomer. It is commercially available as the megluminesalt, sodium salt, or as fixed combinations of the two saltforms. These triiodobenzoic acid salts contain 47% organicallybound iodine.
Numerous products with various concentrations of one ortwo of the salt forms are available for various imaging procedures.Indicated uses include angiography, venography,excretory urography, retrograde cystourethrography, retrogradeor ascending pyelography, operative, T-tube, or percutaneoustranshepatic cholangiography, splenoportography,arthrography; discography, radiographic examinationof the GI tract when barium sulfate is contraindicated (i.e.,suspected perforation of the GI tract), adjunct contrast enhancementin CT of the torso (dual contrast study), and hysterosalpingography.
DIATRIZOIC ACID Preparation Products And Raw materials
Raw materialsACETYL IODIDE-->3,5-Diaminobenzoic acid-->Sodium hydroxide-->Hydrogen-->2-Chloro-3,5-dinitrobenzoic acid-->Iodine monochloride
Preparation ProductsDiatrizoate sodium
Diatrizoic Acid Dihydrate MEGLUMINE DIATRIZOATE Diatrizoate sodium Ioversol methylglucamine metrizoate Metrizoic acid iosulamide sodium metrizoate Sodium diprotrizoate Lozomic acid METHYL 3,5-DIACETAMIDO-2,4,6-TRIIODOBENZOATE Ioxotrizoic acid iosulamide meglumine 2,4,6-TRIIODO-3,5-BIS(N-METHYLACETAMIDO)BENZOIC ACID SODIUM DIATRIZOATE DIHYDRATE Ethyl cartrizoate DIATRIZOIC ACID Amidotrizoic Acid EP Impurity D

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