76820-34-3

Basic information

• Product Name: N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide
• Synonyms: N,N'-BIS(2,3-DIHYDROXYPROPYL)-2,4,6-TRIIODO-5-NITRO-1,3-BENZENEDICARBOXAMIDE;5-Nitro-N,N'-bis(2,3-dihydroxypropyl)isophthalamide;5-NITRO-N,N'-BIS(2,3-DIHYDROXYPROPYL)-1,3-BENZENEDICARBOXAMIDE[IOHEXOL INTERMEDIATE];N,N'-Bis(2,3-Dihydorxypropyl)-5-Benzenediformamide;N,N`-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenediformamide;N,N-Bis-(2,3-dihydroxypropyl)-5-nitroisophthalamide;5-AMINO C N,N'' C BIS (2,3-DIHYDROXYPROPYL)-2,4,6-TRIIODO-1,3-BENZENEDICARBOXAMIDE;N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide
• CAS NO: 76820-34-3
• Molecular Formula: C₁₄H₁₉N₃O₈
• Molecular Weight: 357.32
• Product Categories: Aromatics;Intermediates;Labeling and Diagnostics Reagents
• Mol File: 76820-34-3.mol

Chemical Properties

• Boiling Point: 50ºC
• Flash Point: >230ºC
• Appearance: White or slight yellow crystal powder
• Density: 1.189 g/mL
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide(76820-34-3)
• EPA Substance Registry System: N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide(76820-34-3)

Safety Data

• Hazardous Substances Data: 76820-34-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide is used as an active pharmaceutical ingredient for the preparation of X-ray contrast agents. Its unique chemical properties allow it to enhance the visibility of internal structures during X-ray imaging procedures, aiding in the diagnosis and monitoring of various medical conditions.
Used in Radiology:
In the field of radiology, N,N'-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide serves as a crucial component in the formulation of X-ray contrast agents. These agents are essential for improving the contrast between different tissues and organs during X-ray examinations, facilitating more accurate diagnoses and treatment planning.

Upstream product

• 616-30-8 3-Amino-1,2-propanediol 
• 13290-96-5 dimethyl 5-nitroisophthalate 

Downstream Products

• 76820-35-4 5-Amino-N,N'-bis[2,3-dihydroxypropyl]-1,3-benzenedicarboxamide 
• 76801-93-9 5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide 
• 31127-80-7 N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide 
• 66108-95-0 iohexol 
• 92339-11-2 iodixanol 

Relevant articles and documents

An intermediate of iodoxanol and a method for preparing iodixanol thereof

The present invention provides a method for preparing iodoxasol intermediates of iodoxaol, the intermediate formula VI of iodkesarol VI: 5,5'-[(2-hydroxy-1,3-propanedioxy)bis (acetylimino)] bis [N,N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide], iodized by formula VI to obtain iodoxaol finished products; the present invention provides a new synthetic idea of first forming a dimer and then iodizing, The prepared iodoxaol finished product: the total impurity content ≤ 1.0%, the impurity G content ≤0.5%; the method of the present invention has mild reaction conditions, low damage to the equipment, simple process, green environmental protection and low cost, can ensure the continuous production of high-quality products, has a high application value, suitable for industrial production.

Contrast medium of the impurity F synthetic method and its impurity G contrast medium, impurity H and impurity M application in the synthesis of

The invention relates to a synthesis method of contrast medium impurities, in particular to a contrast medium impurity F synthetic method and its in the contrast medium impurity G, impurity H and M application in the synthesis of the impurity, which belongs to the field of medical technology. The method is to 5 - nitro - 1, 3 - benzene dicarboxylic acid dimethyl ester (formula 2 compound) and 2, 3 - dihydroxy propylamine as raw materials of formula 3 compound, type 3 compound with hydrogen reduction reaction [...] 4 compound, of formula 4 with a compound obtained by reaction of the impurity F [...] contrast medium. The invention relates to 5 - nitro - 1, 3 - benzene dicarboxylic acid dimethyl ester (formula 2 compound) as the starting material, the synthesis of 5 - amino - N, double-N' - (2, 3 - dihydroxy-propyl) - diiodo - 1, 3 - benzene dicarboxylic amide (formula 1 compounds) and then to of formula 1 as the starting material for the synthesis of impurity G, impurity H and impurity M, for the contrast medium quality control to provide acceptable impurity reference substance.

Synthesis of N1,N3-BIS(2,3-DIHYDROXYPROPYL)-5-NITROISOPHTHALAMIDE

The present disclosure generally relates to a new process for the preparation of high purity 5-nitro-isophthalamide compounds, which are useful as intermediates for the preparation of imaging agents, such as iodinated x-ray contrast imaging agents like ioversol, iohexyl and iopamidol.

Formation of N,O-acetalsin the production of x-ray contrast agents

Acetylation of 1 with acetic anhydride, an important step in the preparation of iohexol, gave the corresponding acetanilide and minor amounts of a few byproducts, whose structures have been elucidated. Among the byproducts were some 1,3-oxazolidines which survived when the reaction was quenched by adding methanol and water under strong acidic conditions.

IODINATION PROCESS FOR THE PREPARATION OF 3,5-DISUBSTITUTED-2,4,6-TRIIODO AROMATIC AMINES COMPOUNDS

The invention discloses a improved process for the preparation of 3,5-disubstituted- 2,4,6-triiodo aromatic amines of formula (II), wherein R1 and R2 are defined as herein. The compounds of formula (II) are the key intermediates for the synthesis of a series of non-ionic contrast agents such as Iopamidol, Iohexol and Iodixanol. The process comprises reacting chlorine-free iodinating reagents with 3,5-disubstituted-2,4,6-triiodo aromatic amines to obtain 3,5-disubstituted-2,4,6-triiodo aromatic amines of formula (II), wherein the molar yield of the iodination reaction can reach to 89%.

New brominated compounds as contrast media for X-ray mammography

The invention regards new brominated compounds containing one or two phenyl rings with favorable physico-chemical properties, good tolerance profile, stability and suitable pharmacokinetic profile as contrast media for X-ray mammography, their pharmaceutical formulations and radiological application. The described new bromine contrast media will increase the sensitivity and specificity of X-ray mammography especially in problematic cases. The new contrast media have a higher X-ray absorption than iodine in the energy range used by mammography, a high hydrophilicity, lower toxicity and better tolerance profile than corresponding iodinated compounds.

Chemical compounds

Compounds of the formula: STR1 wherein R represents the group --CH2 CH2 OH or --CH2 CHOHCH2 OH, particularly in racemic or optically active form, are employed as active ingredients in X-ray contrast agents for intracerebral, but particularly for vascular use. The compounds are prepared by reacting 5-(N-acetamido)-2,4,6-triiodo-N,N'-bis-(2,3-dihydroxypropyl)isophthalamide or an O-acetyl derivative thereof with an appropriate hydroxyalkylating agent and subsequently, if necessary, hydrolysing any unwanted O-acetyl groups.

N,N'-Bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-keto-L-gulonamido)isophthalamide and radiological compositions containing same

Novel X-ray contrast agents, i.e., N,N'-bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-keto-L-gulonamido)isophthalamide, and intermediates.