Dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate

Base Information

• Chemical Name: Dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate
• CAS No.: 154921-11-6
• Molecular Formula: C10H8I3NO4
• Molecular Weight: 586.891
• DSSTox Substance ID: DTXSID20438780
• Wikidata: Q82254602
• Mol file: 154921-11-6.mol

Synonyms:154921-11-6;DIMETHYL 5-AMINO-2,4,6-TRIIODO-1,3-BENZENEDICARBOXYLATE;dimethyl 5-amino-2,4,6-triiodoisophthalate;Dimethyl 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylate;1,3-Benzenedicarboxylic acid, 5-amino-2,4,6-triiodo-, 1,3-dimethyl ester;DTXSID20438780;AKOS025243525;AS-75618;dimethyl5-amino-2,4,6-triiodoisophthalate;dimethyl 5-amino-2,4,6-trllodo-1,3-benzenedicarboxylate

Chemical Property of Dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate

Chemical Property:

• Boiling Point: 500.4±50.0 °C(Predicted)
• PKA: -2.61±0.10(Predicted)
• PSA: 78.62000
• Density: 2.511±0.06 g/cm3(Predicted)
• LogP: 3.23700
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 586.7588
• Heavy Atom Count: 18
• Complexity: 311

Purity/Quality:

98%Min ^*data from raw suppliers

Dimethyl5-amino-2,4,6-triiodoisophthalate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C(=C(C(=C1I)N)I)C(=O)OC)I

Technology Process of Dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate

There total 3 articles about Dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2,4,6-triiodo-5-aminoisophthalic acid (35453-19-1) → dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate (154921-11-6)

Guidance literature:

In methanol; diethyl ether; 1.) O deg C, 2 h, 2.) r.t., overnight;

DOI:10.1021/jo00085a023

Reference yield: 95.0%

methanol (67-56-1) + 2,4,6-triiodo-5-aminoisophthalic acid (35453-19-1) → dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate (154921-11-6)

Guidance literature:

With sulfuric acid; for 4h; Reagent/catalyst; Reflux; Large scale;

Reference yield:

5-aminoisophthalic acid (99-31-0) → dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate (154921-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / aq. potassium iododichloride / H₂O / 18 h / 55 - 60 °C

2: 98 percent / methanol; diethyl ether / 1.) O deg C, 2 h, 2.) r.t., overnight

With potassium dichloroiodate; In methanol; diethyl ether; water;

DOI:10.1021/jo00085a023

upstream raw materials:

diazomethane

2,4,6-triiodo-5-aminoisophthalic acid

5-aminoisophthalic acid

methanol

Downstream raw materials:

2,4,6-Triiodo-5-isocyanato-isophthalic acid dimethyl ester

iopromide

iobitridol

dimethyl 2,4,6-triiodo-5-<<(oxiranylmethoxy)carbonyl>amino>-1,3-benzenedicarboxylate

Refernces

• 1、 Pillai, K. M. R.,Diamantidis, G.,Duncan, L.,Ranganathan, R. S.. "Heterocyclic Nonionic X-ray Contrast Agents. 3. The Synthesis of 5--2,4,6-triiodo-1,3-benzenedicarboxamide Derivatives". . p. 1344 - 1350. Retrieved 2007/10/02.