4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate

Base Information

• Chemical Name: 4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate
• CAS No.: 201282-63-5
• Molecular Formula: C₉H₇IN₂O₃
• Molecular Weight: 318.071
• European Community (EC) Number: 804-865-2
• Mol file: 201282-63-5.mol

Synonyms:201282-63-5;4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate;4-iodo-3-(4-methoxyphenyl)oxadiazol-3-ium-5-olate;AKOS025392247;AS-1013;4-iodo-3-(4-methoxyphenyl)-3H-1lambda4,2,3-oxadiazol-1-ylium-5-olate

Chemical Property of 4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 317.95014
• Heavy Atom Count: 15
• Complexity: 212

Purity/Quality:

4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)[N+]2=NOC(=C2I)[O-]

Technology Process of 4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate

There total 3 articles about 4-Iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate 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: 92.0%

3-(p-anisyl)sydnone (3815-80-3) → 4-iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate (201282-63-5)

Guidance literature:

With N-iodo-succinimide; acetic acid; at 20 ℃;

DOI:10.1021/jacs.8b02493

Reference yield:

4-methoxy-aniline (104-94-9) → 4-iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate (201282-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; sodium acetate; sodium cyanoborohydride / methanol / 1 h / 0 - 25 °C

2.1: tert.-butylnitrite / tetrahydrofuran / 0.5 h / 25 °C

2.2: 1 h / 25 °C

3.1: N-iodo-succinimide; acetic acid / 25 °C

With N-iodo-succinimide; tert.-butylnitrite; sodium acetate; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1002/anie.201606495

Reference yield:

N-(4-methoxy)phenylglycine ethyl ester (50845-77-7) → 4-iodo-3-(4-methoxyphenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate (201282-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1: water; lithium hydroxide / tetrahydrofuran / 20 °C

2: tert.-butylnitrite / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: N-iodo-succinimide; acetic acid / 20 °C

With N-iodo-succinimide; tert.-butylnitrite; water; acetic acid; lithium hydroxide; In tetrahydrofuran;

DOI:10.1021/jacs.8b02493

upstream raw materials:

3-(p-anisyl)sydnone

4-methoxy-aniline

N-(4-methoxy)phenylglycine ethyl ester

Downstream raw materials:

5-iodo-1-(4-methoxyphenyl)-3-phenyl-1H-pyrazole

1-(4-methoxy-3-nitrophenyl)-3-phenyl-5-trifluoromethyl-1H-pyrazole

1-(p-methoxyphenyl)-3-cyclopropyl-5-trifluoromethyl-1H-pyrazole

1-(p-methoxyphenyl)-3-n-butyl-5-trifluoromethyl-1H-pyrazole

Refernces

• 1、 Liu, Hui,Audisio, Davide,Plougastel, Lucie,Decuypere, Elodie,Buisson, David-Alexandre,Koniev, Oleksandr,Kolodych, Sergii,Wagner, Alain,Elhabiri, Mourad,Krzyczmonik, Anna,Forsback, Sarita,Solin, Olof,Gouverneur, Véronique,Taran, Frédéric. "Ultrafast Click Chemistry with Fluorosydnones". supporting information. p. 12073 - 12077. Retrieved 2016/11/16.
• 2、 Delaunay, Thierry,Es-Sayed, Mazen,Vors, Jean-Pierre,Monteiro, Nuno,Balme, Genevieve. "Facile access to 3,5-dihalogenated pyrazoles by sydnone cycloaddition and their versatile functionalization by Pd-catalyzed cross-coupling processes". scheme or table. p. 3837 - 3848. Retrieved 2011/09/12.