60166-98-5

Basic information

• Product Name: IOPAMIDOL RELATED COMPOUND A (50 MG) (N,N'-BIS-(1,3-DIHYDROXY-2-PROPYL)-5-AMINO-2,4,6-TRIIO-DOISO-PHTHALAMIDE)
• Synonyms: IOPAMIDOL RELATED COMPOUND A (50 MG) (N,N'-BIS-(1,3-DIHYDROXY-2-PROPYL)-5-AMINO-2,4,6-TRIIO-DOISO-PHTHALAMIDE);Iopamidol Related Compound A (50 mg) (N,N’- Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triio- doiso-phthalamide);5-AMino-2,4,6-triiodisophthalsure-[N,N'-bis(2-hydroxy-1-hydroxyMethylethyl)]-diaMid;5-AMino-N,N'-bis[2-hydroxy-1-(hydroxyMethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxaMide;IopaMidol Related CoMpound A;5-Amino-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodobenzene-1,3-dicarboxamide;N,N′-Bis(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide;N,N′-Bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-amino-2,4,6-triiodoisophthalamide
• CAS NO: 60166-98-5
• Molecular Formula: C₁₄H₁₈I₃N₃O₆
• Molecular Weight: 705.02263
• Mol File: 60166-98-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 688.7±55.0 °C(Predicted)
• Appearance: /
• Density: 2.386±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly)
• PKA: 10.98±0.46(Predicted)
• CAS DataBase Reference: IOPAMIDOL RELATED COMPOUND A (50 MG) (N,N'-BIS-(1,3-DIHYDROXY-2-PROPYL)-5-AMINO-2,4,6-TRIIO-DOISO-PHTHALAMIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: IOPAMIDOL RELATED COMPOUND A (50 MG) (N,N'-BIS-(1,3-DIHYDROXY-2-PROPYL)-5-AMINO-2,4,6-TRIIO-DOISO-PHTHALAMIDE)(60166-98-5)
• EPA Substance Registry System: IOPAMIDOL RELATED COMPOUND A (50 MG) (N,N'-BIS-(1,3-DIHYDROXY-2-PROPYL)-5-AMINO-2,4,6-TRIIO-DOISO-PHTHALAMIDE)(60166-98-5)

Safety Data

• Hazardous Substances Data: 60166-98-5(Hazardous Substances Data)

Usage

Uses

5-Amino-N,N''-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (Iopamidol EP Impurity A) is an impurity in the synthesis of Iopamidol (I735600), a nonionic radiocontrast medium. Diagnostic aid (radiopaque medium).

Upstream product

• 99-31-0 5-aminoisophthalic acid 
• 35453-19-1 2,4,6-triiodo-5-aminoisophthalic acid 
• 25351-79-5 5-amino-isophthalic acid dibutyl ester 
• 10552-75-7 dibutyl 5-nitroisophthalate 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 
• 267881-76-5 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide 
• 13290-96-5 dimethyl 5-nitroisophthalate 
• 60166-97-4 N,N'-bis-(2-hydroxy-1-hydroxymethylethyl)-5-nitroisophthalamide 
• 534-03-2 serinol 
• 37441-29-5 5-amino-2,4,6-triiodoisophthalic acid dichloride 

Downstream Products

• 60166-93-0 Iopamidol 
• 87932-07-8 5-acetylamino-N,N'-bis(1,3-dihydroxy-2-propyl)-2,4,6-triiodoisophthalamide 
• 148051-08-5 N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide 
• 154921-15-0 N,N'-bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<4-(hydroxymethyl)-2-oxo-3-oxazolidinyl>-1,3-benzenedicarboxamide 
• 154921-13-8 <3,5-bis<<<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>amino>carbonyl>-2,4,6-triiodophenyl>carbamic acid, oxyranylmethyl ester 
• 189242-93-1 Acetic acid 3-acetoxy-2-[3-(2-acetoxy-1-acetoxymethyl-ethylcarbamoyl)-2,4,6-triiodo-5-isocyanato-benzoylamino]-propyl ester 

Relevant articles and documents

MECHANOCHEMICAL SYNTHESIS OF RADIOGRAPHIC AGENTS INTERMEDIATES

The present invention generally relates to a process using a mechanochemical approach exploiting the mechanical milling of reactants for the manufacturing of acetyl Iopamidol and, more generally, of key intermediates of radiographic contrast agents, and of the contrast agents themselves.

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%.

Heterocyclic Nonionic X-ray Contrast Agents. 3. The Synthesis of 5--2,4,6-triiodo-1,3-benzenedicarboxamide Derivatives

The syntheses of 2,4,6-triiodo-1,3-benzenedicarboxamide analogs, 12c, 12e, and 17c, of interest as X-ray diagnostic agents and in which the 5 position is linked to the N atom of a 4-(hydroxymethyl)-oxazolidin-2-one moiety, are described.The heterocycle was built from suitably protected 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid derivatives by a three-step procedure consisting of (1) phosgene treatment to obtain the corresponding isocyanates, (2) phenylmercuric chloride-catalyzed addition of glycidol (10) resulting in glycidil carbamates, and (3) pyridine-catalyzed intramolecular N-alkylation, followed by deprotection, to obtain the oxazolidin-2-ones.The intramolecular N-alkylation reaction was highly regioselective and was not appreciably accompanied by O-alkylation products under the experimental conditions employed.The two carboxamide nitrogen atoms in the intermediates and end products carry either 2,3-dihydroxypropyl or 1,3-dihydroxypropyl residues.These highly congested benzenoid compounds exhibited interesting NMR spectral features due to atropisomerism arising from hindrance to free rotation about the three single bonds that link the aromatic moiety to the N-containing functionalities.