5-Iodoisatin

Base Information

• Chemical Name: 5-Iodoisatin
• CAS No.: 20780-76-1
• Molecular Formula: C8H4INO2
• Molecular Weight: 273.03
• Hs Code.: 29337900
• European Community (EC) Number: 244-035-1
• NSC Number: 92515
• DSSTox Substance ID: DTXSID50174866
• Nikkaji Number: J225.333J
• Wikidata: Q83045023
• ChEMBL ID: CHEMBL325480
• Mol file: 20780-76-1.mol

Synonyms:5-iodoisatin

Chemical Property of 5-Iodoisatin

Chemical Property:

• Appearance/Colour: red solid
• Melting Point: 276-280 °C(lit.)
• Refractive Index: 1.704
• PKA: 8.87±0.20(Predicted)
• PSA: 46.17000
• Density: 2.106 g/cm³
• LogP: 1.56400
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Light Sensitive
• Water Solubility.: Soluble acetone, acetic acid, ethanol. Insoluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 272.92868
• Heavy Atom Count: 12
• Complexity: 241

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Iodoisatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1I)C(=O)C(=O)N2
• Uses: 5-Iodoisatin undergoes condensation reaction with phenol yields 5-iodophenolisatin, malonic acid yields 6-iodo-2-quinolone-4-carboxylic acid.

Technology Process of 5-Iodoisatin

There total 10 articles about 5-Iodoisatin 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: 97.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 5-iodoisatin (20780-76-1)

Guidance literature:

With K⁽¹⁺⁾*Cl₂I^(1-); In methanol; water; at 20 ℃; for 48h;

DOI:10.1016/S0040-4039(01)00105-8

Reference yield: 87.0%

5-iodo-2,3-dihydro-1H-indole (114144-16-0) → 5-iodoisatin (20780-76-1)

Guidance literature:

With iodine pentoxide; In dimethyl sulfoxide; at 80 ℃;

DOI:10.1016/j.tetlet.2017.03.060

Reference yield: 83.0%

p-iodoisonitrosoacetanilide (60313-92-0) → 5-iodoisatin (20780-76-1)

Guidance literature:

With sulfuric acid; at 65 - 80 ℃; for 0.25h;

DOI:10.1016/j.ejmech.2015.01.034

upstream raw materials:

p-iodoisonitrosoacetanilide

indole-2,3-dione

chloral hydrate

p-aminoiodobenzene

Downstream raw materials:

5-iodoindazole-3-carboxylic acid

3-(2-ethoxy-phenyl)-3-hydroxy-5-iodo-1,3-dihydro-indol-2-one

methyl 5-iodo-1H-indazole-3-carboxylate

N-benzyl-5-iodoisatin

Refernces

• 1、 Carrera, Elisa I.,McCormick, Theresa M.,Kapp, Marius J.,Lough, Alan J.,Seferos, Dwight S.. "Thermal and photoreductive elimination from the tellurium center of π-conjugated tellurophenes". . p. 13779 - 13790. Retrieved 2013.
• 2、 Bondarenko, Oksana B.,Karetnikov, Georgy L.,Komarov, Arseniy I.,Pavlov, Aleksandr I.,Nikolaeva, Svetlana N.. "R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond". supporting information. p. 322 - 332. Retrieved 2021/01/14.
• 3、 Santos, Iara S.,Guerra, Fabiana S.,Bernardino, Lucas F.,Fernandes, Patrícia D.,Hamerski, Lidilhone,Silva, Bárbara V.. "A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity". . p. 198 - 209. Retrieved 2018/12/13.