5-Iodoisobenzofuran-1,3-dione

Base Information

• Chemical Name: 5-Iodoisobenzofuran-1,3-dione
• CAS No.: 28418-89-5
• Molecular Formula: C₈H₃IO₃
• Molecular Weight: 274.015
• DSSTox Substance ID: DTXSID40570656
• Wikidata: Q82458175
• Mol file: 28418-89-5.mol

Synonyms:5-iodoisobenzofuran-1,3-dione;28418-89-5;5-Iodo-2-benzofuran-1,3-dione;5-iodo-1,3-dihydro-2-benzofuran-1,3-dione;4-Jodphthalsaureanhydrid;4-iodophthalic anhydride;SCHEMBL2207735;DTXSID40570656;HAXOVWANMPEGGM-UHFFFAOYSA-N;CS-0199073;E76997;EN300-21628337

Chemical Property of 5-Iodoisobenzofuran-1,3-dione

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 273.91269
• Heavy Atom Count: 12
• Complexity: 239

Purity/Quality:

98% ^*data from raw suppliers

5-Iodoisobenzofuran-1,3-dione 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1I)C(=O)OC2=O

Technology Process of 5-Iodoisobenzofuran-1,3-dione

There total 5 articles about 5-Iodoisobenzofuran-1,3-dione 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%

4-iodophthalic acid (6301-60-6) → 4-iodophthalic anhydride (28418-89-5)

Guidance literature:

With acetic anhydride; at 100 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c9ta03869h

Reference yield:

para-iodoanisole (696-62-8) + trimellitic anhydride acid chloride (1204-28-0) → 4-iodophthalic anhydride (28418-89-5) + 4-methoxy-benzoyl chloride (100-07-2)

Guidance literature:

With (Xantphos)Pd(4-C₆H₄NO₂)(I); In benzene; at 110 ℃; for 20h; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.8b06605

Reference yield:

3,4-dimethyliodobenzene (31599-61-8) → 4-iodophthalic anhydride (28418-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; potassium permanganate / water / 24 h / Inert atmosphere; Schlenk technique; Reflux

2: acetic anhydride / 24 h / 100 °C / Inert atmosphere; Schlenk technique

With pyridine; potassium permanganate; acetic anhydride; In water;

DOI:10.1039/c9ta03869h

upstream raw materials:

4-iodophthalic acid

2-amino-5-iodobenzoic acid

para-iodoanisole

trimellitic anhydride acid chloride

Downstream raw materials:

4,4'-oxydiphthalic dianhydride

2,3',3,4'-biphenyltetracarboxylic acid dianhydride

4-hydroxyphthalic acid

Refernces

• 1、 Furukawa, Seiichi,Yasuda, Takuma. "Strategic end-halogenation of π-conjugated small molecules enabling fine morphological control and enhanced performance of organic solar cells". supporting information. p. 14806 - 14815. Retrieved 2019/06/24.