4,5-Diiodo-1H-imidazole

Base Information

• Chemical Name: 4,5-Diiodo-1H-imidazole
• CAS No.: 15813-09-9
• Molecular Formula: C3H2I2N2
• Molecular Weight: 319.871
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID90378422
• Nikkaji Number: J982.912A
• Wikidata: Q72467196
• Mol file: 15813-09-9.mol

Synonyms:4,5-Diiodo-1H-imidazole;15813-09-9;4,5-Diiodoimidazole;1H-IMIDAZOLE, 4,5-DIIODO-;4(5)-Diiodo-1H-imidazole;MFCD00963878;diiodoimidazole;C3H2I2N2;4,5-triiodo-1H-imidazole;SCHEMBL585892;AMY760;DTXSID90378422;BCP17505;BBL029092;CL2231;STK983919;AKOS005647197;AB07820;AC-7374;CS-W002714;PS-7050;NCGC00342537-01;SY005943;FT-0649180;EN300-103476;AB01334589-02;A809900;AT-057/15269007;W-200542;F0001-0563

Chemical Property of 4,5-Diiodo-1H-imidazole

Chemical Property:

• Melting Point: 197-198 °C
• Refractive Index: 1.616
• Boiling Point: 436.9 °C at 760 mmHg
• PKA: 9.31±0.10(Predicted)
• Flash Point: 218 °C
• PSA: 28.68000
• Density: 3.042 g/cm³
• LogP: 1.61890
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 319.83074
• Heavy Atom Count: 7
• Complexity: 68

Purity/Quality:

99% ^*data from raw suppliers

4,5-Diiodo-1H-imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1)I)I
• Uses: suzuki reaction

Technology Process of 4,5-Diiodo-1H-imidazole

There total 4 articles about 4,5-Diiodo-1H-imidazole 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: 99.0%

1H-imidazole (288-32-4) → 4,5-diiodo-1H-imidazole (15813-09-9)

Guidance literature:

With iodine; potassium iodide; sodium hydroxide; In water; at 20 ℃; for 3h;

DOI:10.1016/j.ejmech.2017.09.025

Reference yield: 99.0%

5-imidazolecarboxaldehyde (3034-50-2) → 4,5-diiodo-1H-imidazole (15813-09-9)

Guidance literature:

With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; sulfuric acid; potassium iodide; In water; at 0 ℃; for 0.0166667h;

DOI:10.1002/adsc.201200723

Reference yield: 90.0%

2,4,5-triiodoimidazole (1746-25-4) → 4,5-diiodo-1H-imidazole (15813-09-9)

Guidance literature:

With sodium thiophenolate; In isopropyl alcohol; for 4h; Heating;

upstream raw materials:

1H-imidazole

2,4,5-triiodoimidazole

5-imidazolecarboxaldehyde

Downstream raw materials:

1-benzyloxymethyl-4,5-diiodo-1H-imidazole

5-Iodo-1-methyl-4-nitroimidazole

4-Iodo-1-methyl-5-nitroimidazole

4-iodoimidazole

Refernces

• 1、 Sandtorv, Alexander H.,Bj?rsvik, Hans-René. "Scope and Mechanistic Limitations of a Sonogashira Coupling Reaction on an Imidazole Backbone". . p. 4658 - 4666. Retrieved 2015.
• 2、 Desforges, Gwéna?lle,Bossert, Cécile,Montagne, Cyril,Joseph, Beno?t. "Synthesis of imidazolo[5,4-b]carbazole-4,10-quinones". . p. 1306 - 1308. Retrieved 2004.
• 3、 ?í?ková, Martina,?aman, David,Koval, Du?an,Ka?i?ka, Václav,Klepetá?ová, Blanka,Císa?ová, Ivana,Teply, Filip. "Modular synthesis of helicene-like compounds based on the imidazolium motif". . p. 5681 - 5685. Retrieved 2014.
• 4、 Sandmann, Nikolas,Defayay, Denise,Hepp, Alexander,Müller, Jens. "Metal-mediated base pairing in DNA involving the artificial nucleobase imidazole-4-carboxylate". . p. 85 - 93. Retrieved 2019.
• 5、 Lohbeck, Jasmin,Miller, Aubry K.,Morgen, Michael. "Mild mono-acylation of 4,5-diiodoimidazole: Preparation of 1-(5-iodo-1H-imidazole-4-yl)pent-4-en-1-one". . p. 171 - 193. Retrieved 2021/07/19.