Diazene, bis(4-iodophenyl)-, 1-oxide

Base Information

• Chemical Name: Diazene, bis(4-iodophenyl)-, 1-oxide
• CAS No.: 19618-18-9
• Molecular Formula: C₁₂H₈I₂N₂O
• Molecular Weight: 450.017
• DSSTox Substance ID: DTXSID10456418
• Mol file: 19618-18-9.mol

Synonyms:Diazene, bis(4-iodophenyl)-, 1-oxide;19618-18-9;DTXSID10456418;(4-iodophenyl)-(4-iodophenyl)imino-oxidoazanium;3,3'-diiodazoxybenzol;4,4'-diiodoazoxybenzene

Chemical Property of Diazene, bis(4-iodophenyl)-, 1-oxide

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 449.87261
• Heavy Atom Count: 17
• Complexity: 270

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N=[N+](C2=CC=C(C=C2)I)[O-])I

Technology Process of Diazene, bis(4-iodophenyl)-, 1-oxide

There total 3 articles about Diazene, bis(4-iodophenyl)-, 1-oxide 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: 81.0%

p-nitrobenzene iodide (636-98-6) → 1,2-bis(4-iodophenyl)diazene oxide (19618-18-9,21650-68-0,603121-28-4)

Guidance literature:

With copper(l) iodide; (1R,1'R,2S,2'S)-1,1'-(propane-1,3-diyl)bis(2-((2,4,6-trimethoxyphenyl)carbamoyl)pyrrolidine 1-oxide); dimethyl sulfoxide; sodium hydroxide; In water; at 80 ℃; for 12h; diastereoselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1016/j.tetlet.2018.02.064

Reference yield:

m-iodonitrobenzene (645-00-1) + benzyl alcohol (100-51-6,185532-71-2) → 1-(benzyloxy)-3-iodobenzene (107623-21-2) + 1,2-bis(4-iodophenyl)diazene oxide (19618-18-9,21650-68-0,603121-28-4) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In various solvent(s); at 50 ℃; for 40h; Title compound not separated from byproducts;

Reference yield:

1-iodo-4-nitrosobenzene (13125-93-4) → 1,2-bis(4-iodophenyl)diazene oxide (19618-18-9,21650-68-0,603121-28-4) + (E)-1,2-bis(4-iodophenyl)diazene (21650-53-3)

Guidance literature:

With iron pentacarbonyl; In tetrahydrofuran; at 30 ℃; for 3h; Title compound not separated from byproducts; Irradiation;

DOI:10.1016/0022-328X(89)80121-4

upstream raw materials:

1-iodo-4-nitrosobenzene

m-iodonitrobenzene

benzyl alcohol

p-nitrobenzene iodide

Refernces

• 1、 Chen, Zhichao,Qiu, Yatao,Wu, Xiaoxing,Ni, Yong,Shen, Li,Wu, Jun,Jiang, Sheng. "Highly selective reduction of nitrobenzenes to azoxybenzenes with a copper catalyst". supporting information. p. 1382 - 1384. Retrieved 2018/03/06.
• 2、 Herndon, James W.,McMullen, Leonard A.. "Metathesis and reduction reactions of nitroso compounds with metal carbenes and metal carbonyls". . p. 83 - 102. Retrieved 2007/10/02.