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Iomeprol, also known as Iomeron, is a non-ionic, water-soluble, iodinated benzenedicarboxamide compound. It has N-substituted carbamoyl groups at the 1and 3-positions, iodo substituents at the 2-, 4-, and 6-positions, and a glycoloyl(methyl)amino group at the 5-position. Iomeprol is a white solid and is used as a diagnostic aid in the medical field.

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  • 78649-41-9 Structure
  • Basic information

    1. Product Name: IOMEPROL
    2. Synonyms: IOMEPROL;1,3-Benzenedicarboxamide, N,N'-bis(2,3-dihydroxypropyl)-5-[(hydroxyacetyl)methylamino]-2,4,6-triiodo-;Imeron;Iomeron 350;Iomeron;N,N'-bis(2,3-dihydroxypropyl)-5-[(hydroxyacetyl)methylamino]-2,4,6-triiodo-1,3-benzenedicarboxamide;N,N'-Bis(2,3-dihydroxypropyl)-5-[methyl(hydroxyacetyl)amino]-2,4,6-triiodoisophthalamide;N,N'-bis(2,3-dihydroxypropyl)-5-[(hydroxyacetyl)MethylaMino]-2,4,6-triiodo -
    3. CAS NO:78649-41-9
    4. Molecular Formula: C17H22I3N3O8
    5. Molecular Weight: 777.09
    6. EINECS: 1533716-785-6
    7. Product Categories: pharmacetical;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 78649-41-9.mol
  • Chemical Properties

    1. Melting Point: 263-265?C
    2. Boiling Point: 813.185 °C at 760 mmHg
    3. Flash Point: 445.599 °C
    4. Appearance: White Solid
    5. Density: d420 1.166; d437 1.161; d420 1.334; d437 1.329; d420 1.446; d437
    6. Vapor Pressure: 5.95E-28mmHg at 25°C
    7. Refractive Index: nD20 1.3828; nD20 1.4327; nD20 1.4660
    8. Storage Temp.: -20°C Freezer
    9. Solubility: DMSO (Slightly), Methanol (Slightly)
    10. PKA: 11.36±0.46(Predicted)
    11. CAS DataBase Reference: IOMEPROL(CAS DataBase Reference)
    12. NIST Chemistry Reference: IOMEPROL(78649-41-9)
    13. EPA Substance Registry System: IOMEPROL(78649-41-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 78649-41-9(Hazardous Substances Data)

78649-41-9 Usage

Uses

Used in Medical Imaging:
Iomeprol is used as a radiopaque medium for various diagnostic imaging procedures, such as X-ray computed tomography (CT) and angiography. It enhances the visibility of blood vessels and internal organs by increasing the contrast between different tissues, allowing for more accurate diagnosis and assessment of various conditions.
Used in Pharmaceutical Industry:
Iomeprol is also used in the pharmaceutical industry as an active pharmaceutical ingredient (API) for the development of contrast agents. These agents are essential for improving the quality and accuracy of medical imaging, which is crucial for early detection and treatment of various diseases and conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 78649-41-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,8,6,4 and 9 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 78649-41:
(7*7)+(6*8)+(5*6)+(4*4)+(3*9)+(2*4)+(1*1)=179
179 % 10 = 9
So 78649-41-9 is a valid CAS Registry Number.
InChI:InChI=1/C17H22I3N3O8/c1-23(9(29)6-26)15-13(19)10(16(30)21-2-7(27)4-24)12(18)11(14(15)20)17(31)22-3-8(28)5-25/h7-8,24-28H,2-6H2,1H3,(H,21,30)(H,22,31)

78649-41-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name iomeprol

1.2 Other means of identification

Product number -
Other names 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[(2-hydroxyacetyl)-methylamino]-2,4,6-triiodobenzene-1,3-dicarboxamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:78649-41-9 SDS

78649-41-9Synthetic route

N1,N3-bis(2,3-dihydroxypropyl)-5-(2-hydroxyacetamido)-2,4,6-triiodobenzene-1,3-dicarboxamide
77868-40-7

N1,N3-bis(2,3-dihydroxypropyl)-5-(2-hydroxyacetamido)-2,4,6-triiodobenzene-1,3-dicarboxamide

methyl iodide
74-88-4

methyl iodide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl acetamide at 10 - 60℃; for 16h;95%
With sodium hydroxide In N,N-dimethyl acetamide at 10 - 60℃;95%
2-((3,5-bis((2,3-dihydroxypropyl)carbamoyl)-2,4,6-triiodophenyl)(methyl)amino)-2-oxoethylacetate

2-((3,5-bis((2,3-dihydroxypropyl)carbamoyl)-2,4,6-triiodophenyl)(methyl)amino)-2-oxoethylacetate

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 3h; Reagent/catalyst; Temperature;90%
Multi-step reaction with 2 steps
1: pyridine / 20.5 h / 5 - 20 °C
2: calcium hydroxide / water / 4 h / 20 °C
View Scheme
5-[N-methyl-2-chloroacetamido]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

5-[N-methyl-2-chloroacetamido]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
With sodium acetate In water for 17h; Time; Reflux; Large scale;88%
3-(3-((2-acetoxy-3-acetoxypropyl)carbamoyl)-5-(2-acetoxy-N-methylacetamido)-2,4,6-triiodobenzamido)propane-1,2-diyl diacetate

3-(3-((2-acetoxy-3-acetoxypropyl)carbamoyl)-5-(2-acetoxy-N-methylacetamido)-2,4,6-triiodobenzamido)propane-1,2-diyl diacetate

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
With calcium hydroxide In water at 20℃; for 4h; Reagent/catalyst; Temperature;84%
With sulfuric acid In methanol for 3h; Solvent; Reflux;65%
N,N'-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-5-methylcarbamoylmethoxy-isophthalamide

N,N'-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-5-methylcarbamoylmethoxy-isophthalamide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
With sodium hydroxide In water at 50℃; Smiles rearrangement;81%
5-aminoisophthalic acid
99-31-0

5-aminoisophthalic acid

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sulfuric acid / chloroform / 7 h / 50 - 60 °C / Large scale
2.1: sulfuric acid / 9 h / Reflux; Large scale
3.1: sodium methylate / methanol / 12 h / 5 °C / Reflux
4.1: Iodine monochloride / water / 5 h / 64 - 90 °C / Large scale
4.2: 36 h / 5 - 50 °C / pH 2 / Large scale
5.1: N,N-dimethyl acetamide / 2 h / 10 - 70 °C / Large scale
5.2: 4 h / 30 - 50 °C / Large scale
6.1: sodium acetate / water / 17 h / Reflux; Large scale
View Scheme
5-methylaminoisophthalic acid

5-methylaminoisophthalic acid

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sulfuric acid / 9 h / Reflux; Large scale
2.1: sodium methylate / methanol / 12 h / 5 °C / Reflux
3.1: Iodine monochloride / water / 5 h / 64 - 90 °C / Large scale
3.2: 36 h / 5 - 50 °C / pH 2 / Large scale
4.1: N,N-dimethyl acetamide / 2 h / 10 - 70 °C / Large scale
4.2: 4 h / 30 - 50 °C / Large scale
5.1: sodium acetate / water / 17 h / Reflux; Large scale
View Scheme
5-methylaminoisophthalic acid dimethyl ester
55648-31-2

5-methylaminoisophthalic acid dimethyl ester

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium methylate / methanol / 12 h / 5 °C / Reflux
2.1: Iodine monochloride / water / 5 h / 64 - 90 °C / Large scale
2.2: 36 h / 5 - 50 °C / pH 2 / Large scale
3.1: N,N-dimethyl acetamide / 2 h / 10 - 70 °C / Large scale
3.2: 4 h / 30 - 50 °C / Large scale
4.1: sodium acetate / water / 17 h / Reflux; Large scale
View Scheme
5-methylamino-N, N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide

5-methylamino-N, N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Iodine monochloride / water / 5 h / 64 - 90 °C / Large scale
1.2: 36 h / 5 - 50 °C / pH 2 / Large scale
2.1: N,N-dimethyl acetamide / 2 h / 10 - 70 °C / Large scale
2.2: 4 h / 30 - 50 °C / Large scale
3.1: sodium acetate / water / 17 h / Reflux; Large scale
View Scheme
5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide
76801-93-9

5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap / ethyl acetate / 2 h / Reflux
2: N,N-dimethyl-formamide / 4 h / 40 °C
3: potassium carbonate / acetone / 12 h / -5 - 20 °C
4: sulfuric acid / methanol / 3 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: dmap / ethyl acetate / 2 h / Reflux
2: N,N-dimethyl-formamide / 4 h / 40 °C
3: potassium carbonate / acetone / 5 h / 20 °C
4: sulfuric acid / methanol / 3 h / Reflux
View Scheme
5-amino-N,N'-bis[2,3-bis(acetyloxy)propyl]2,4,6-triiodo-1,3-benzenedicarboxamide
76801-94-0

5-amino-N,N'-bis[2,3-bis(acetyloxy)propyl]2,4,6-triiodo-1,3-benzenedicarboxamide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 4 h / 40 °C
2: potassium carbonate / acetone / 12 h / -5 - 20 °C
3: sulfuric acid / methanol / 3 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 4 h / 40 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: sulfuric acid / methanol / 3 h / Reflux
View Scheme
5-(acetoxyacetylamino)-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide

5-(acetoxyacetylamino)-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 12 h / -5 - 20 °C
2: sulfuric acid / methanol / 3 h / Reflux
View Scheme
N1,N3-bis(2,3-dihydroxypropyl)-5-(2-hydroxyacetamido)-2,4,6-triiodobenzene-1,3-dicarboxamide
77868-40-7

N1,N3-bis(2,3-dihydroxypropyl)-5-(2-hydroxyacetamido)-2,4,6-triiodobenzene-1,3-dicarboxamide

dimethyl sulfate
77-78-1

dimethyl sulfate

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Stage #1: N,N'-bis-(2,3-dihydroxypropyl)-5-(2-hydroxyacetylamino)-2,4,6-triiodoisophthalamide With calcium chloride In methanol at 70℃; for 3h;
Stage #2: With calcium hydroxide In methanol at 0 - 5℃; for 1h;
Stage #3: dimethyl sulfate In methanol at 0 - 5℃; for 7h; Temperature;
4.21 g
2-((3,5-bis (chlorocarbonyl)-2,4,6-triiodophenyl)amino)-2-oxoethyl acetate
78314-12-2

2-((3,5-bis (chlorocarbonyl)-2,4,6-triiodophenyl)amino)-2-oxoethyl acetate

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / N,N-dimethyl acetamide / 15 h / 15 - 30 °C
2: sodium hydroxide / water / 8 h / 25 - 30 °C
3: sodium hydroxide / N,N-dimethyl acetamide / 16 h / 10 - 60 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / N,N-dimethyl acetamide / 15 h / 15 - 30 °C
2: water; sodium hydroxide / 8 h / 25 - 30 °C
3: sodium hydroxide / N,N-dimethyl acetamide / 10 - 60 °C
View Scheme
5-amino-2,4,6-triiodoisophthalic acid dichloride
37441-29-5

5-amino-2,4,6-triiodoisophthalic acid dichloride

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N,N-dimethyl acetamide / 20.5 h / 20 - 25 °C
2: triethylamine / N,N-dimethyl acetamide / 15 h / 15 - 30 °C
3: sodium hydroxide / water / 8 h / 25 - 30 °C
4: sodium hydroxide / N,N-dimethyl acetamide / 16 h / 10 - 60 °C
View Scheme
Multi-step reaction with 4 steps
1: N,N-dimethyl acetamide / 2.5 h / 20 - 25 °C
2: triethylamine / N,N-dimethyl acetamide / 15 h / 15 - 30 °C
3: water; sodium hydroxide / 8 h / 25 - 30 °C
4: sodium hydroxide / N,N-dimethyl acetamide / 10 - 60 °C
View Scheme
2-((3,5-bis((2,3-dihydroxypropyl)carbamoyl)-2,4,6-triiodophenyl)amino)-2-oxoethyl acetate

2-((3,5-bis((2,3-dihydroxypropyl)carbamoyl)-2,4,6-triiodophenyl)amino)-2-oxoethyl acetate

iomeprol
78649-41-9

iomeprol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 8 h / 25 - 30 °C
2: sodium hydroxide / N,N-dimethyl acetamide / 16 h / 10 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: water; sodium hydroxide / 8 h / 25 - 30 °C
2: sodium hydroxide / N,N-dimethyl acetamide / 10 - 60 °C
View Scheme

78649-41-9Downstream Products

78649-41-9Relevant articles and documents

Synthesis method of iomeprol

-

, (2022/03/27)

The invention relates to a preparation method of iomeprol. The iomeprol is a non-ionic X-ray contrast agent with excellent safety and contrast effect. The invention relates to a synthesis method of iomeprol, which is characterized in that 5-amino-N, N '-bis (2, 3-dihydroxy propyl)-2, 4, 6-triiodo-1, 3-benzene dicarboxamide (compound II) is used as an initial raw material, chloroacetylation, methylation, hydrolysis and hydroxylation reactions are sequentially carried out to synthesize an iomeprol product, and the synthesis route is as follows. The chemical method for preparing iomeprol is realized through the following steps: acylation reaction, methylation reaction, hydrolysis reaction and hydroxylation reaction. The preparation method disclosed by the invention is stable in quality, high in yield, low in cost, small in pollution and easy to realize industrial production.

New Methods for Preparing an Intermediate of Contrast Medium and Methods for Preparing Contrast Medium

-

, (2020/10/07)

A manufacturing method of the present invention reduces treatment processes when manufacturing a contrast medium or an intermediate thereof, and thus generates less waste solvent, thereby being eco-friendly and capable of significantly reducing a manufacturing cost. Therefore, the manufacturing method of the present invention is economical and suitable for mass production since the production cost of the contrast medium can be greatly reduced.

New Methods for Preparing an Intermediate of Contrast Medium and Methods for Preparing Contrast Medium

-

, (2020/10/14)

The present invention relates to a method for preparing an intermediate of contrast agent or contrast agent. Also, the manufacturing cost can be significantly reduced. , The manufacturing method of the present invention can greatly reduce the production cost of contrast agents and is suitable for mass production. (by machine translation)

PROCESS FOR THE PROPARATION OF CONTRAST MEDIUM IOMEPROL

-

Paragraph 0032; 0060-0075, (2020/06/04)

The present invention relates to a method for preparing an X-ray contrast agent iomeprol and, more specifically, to a method for preparing iomeprol by adding an inorganic base, an inorganic chloride, a solvent, etc. to 5-(2-hydroxyacetamido)-N,Nandprime;-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (1b) to induce N-methylation reaction, thereby enabling easy separation and removal of inorganic salts generated during the reaction, without treatment with an ion exchange resin, while reducing the conventional production time, and minimization of the amount of reaction impurities.COPYRIGHT KIPO 2020

preparation method of contrast agent

-

Paragraph 0065; 0078; 0079; 0081; 0082; 0084; 0085, (2018/10/16)

The present invention relates to a method for producing a contrast medium with high purity and high efficiency, and since no methyl iodide and the like are used in a production process, no salt is generated or only a very small amount thereof is generated, and a high purity and high efficiency contrast medium can be produced without complicated purification and washing steps. In addition, a small amount of salt can be easily removed by washing with water.COPYRIGHT KIPO 2018

Novel method for preparing iomeprol

-

, (2018/02/03)

The invention belongs to the technical field of non-ionic X-ray contrast agents, and discloses a novel method for preparing iomeprol. The preparation method comprises the steps of carrying out N-methylation reaction by employing a compound 5-aminoisophthalic acid as a raw material; carrying out esterification reaction; carrying out amidation reaction; carrying out iodination reaction; carrying out chloroacetylation reaction; and finally carrying out hydroxylation reaction to prepare the iomeprol. The preparation method is stable in quality, high in yield, low in cost, environmentally friendly, and easy for realization of industrial mass production.

NOVEL INTERMEDIATE COMPOUND AND PREPARATION PROCESS OF IOMEPROL USING THEREOF

-

, (2018/02/20)

The present invention relates to a novel intermediate compound of iomeprol, a production method thereof, and a method for producing iomeprol using the same. More specifically, the present invention relates to a method for producing iomeprol used as X-ray vascular contrast agents in an economically feasible way with high purity using a novel intermediate N,Nandprime;-bis(2,3-diacetylatepropyl)-5-(2-acetoxy-N-methylacetoamide)-2,4,6-triiodoisophthalamide. The present invention further relates to a purification method thereof.COPYRIGHT KIPO 2017

A PROCESS FOR THE RECOVERY OF IODINE FROM AQUEOUS SOLUTIONS CONTAINING IODINATED ORGANIC COMPOUNDS

-

, (2008/06/13)

A process for the recovery of iodine from mother liquors or wastes containing iodinated organic compounds, by mineralisation of organic iodine and subsequent transformation of the formed iodide into elementary iodine, characterized in that the aqueous solution is concentrated to a suitable volume before the mineralisation step, under atmospheric pressure and at the boiling temperature, and said solution is purified by nanofiltration.

Smiles rearrangement as a tool for the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamides: Main pathway and side reactions

Anelli, Pier Lucio,Brocchetta, Marino,Calabi, Luisella,Secchi, Carlo,Uggeri, Fulvio,Verona, Sandra

, p. 11919 - 11928 (2007/10/03)

In the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamides 1a-h from 2a-h two conditions using stoichiometric amounts of base (method A - aq NaOH at 50°C; method B - MeONa in DMF at r, t.) were used. Yields are good to excellent provided that the right conditions are chosen. Primary amides 2a,b give 1a,b with method B only, whereas with method A extensive hydrolysis of the CONH2 moiety is observed. N-Methyl derivatives 2c,d afford 1c,d with either method. However, with method B long reaction times lead to the formation of large amounts of benzoxazinones, 4c,d. Under the same conditions, the pattern of side products which are formed from N-(hydroxyalkyl)phenoxyacetamides 2e-g is further complicated by: i) intramolecular cyclizations leading to bicyclic (7f,g) and tricyclic structures (5) ii) N-deacylation; iii) double Smiles rearrangement reactions.

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