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.

pka

0.92±0.10(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

500g/L(25 ºC)

Merck 

14,2992

Stability:

Light Sensitive

InChI

InChI=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)

InChIKey

YVPYQUNUQOZFHG-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=C(I)C(NC(C)=O)=C(I)C(NC(C)=O)=C1I

LogP

3.3 at 20℃

EPA Substance Registry System

Benzoic 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 Data

117-96-4(Hazardous Substances Data)

Toxicity

LD50 intravenous in mouse: 8900mg/kg

MSDS

• Language:English Provider:SigmaAldrich

DIATRIZOIC ACID Usage And Synthesis

Chemical Properties

White Solid

Originator

Hypaque Sodium,Winthrop,US,1955

Uses

Diatrizoic 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.

Uses

Density gradient reagent for blood cell seperation. Diagnostic aid (radiopaque medium)

Uses

radiopaque agent

Definition

ChEBI: 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 Process

3,5-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 name

Md (Mallinckrodt); Urovist Sodium (Berlex).

Therapeutic Function

Diagnostic aid (radiopaque medium)

General Description

Diatrizoate 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(117-96-4)Related Product Information

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• METHYL 3,5-DIACETAMIDO-2,4,6-TRIIODOBENZOATE