Oxindole

Base Information

• Chemical Name: Oxindole
• CAS No.: 59-48-3
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Hs Code.: 2933.99
• European Community (EC) Number: 200-429-5
• NSC Number: 274863
• UNII: 0S9338U62H
• DSSTox Substance ID: DTXSID80870389
• Nikkaji Number: J1.393E
• Wikipedia: Oxindole
• Wikidata: Q2018788
• Metabolomics Workbench ID: 54435
• ChEMBL ID: CHEMBL40823
• Mol file: 59-48-3.mol

Synonyms:2-Indolinone(7CI,8CI);Oxindole (6CI);1,3-Dihydro-2H-indol-2-one;1,3-Dihydroindol-2-one;2-Indolone;2-Oxindole;2-Oxo-2,3-dihydroindole;2-Oxoindole;2-Oxoindoline;Indol-2(3H)-one;Indoline-2-one;NSC 274863;Oxindol;

Chemical Property of Oxindole

Chemical Property:

• Appearance/Colour: beige to yellowish-orange or pinkish-brown powder
• Vapor Pressure: 0.000521mmHg at 25°C
• Melting Point: 123-128 °C(lit.)
• Refractive Index: 1.586
• Boiling Point: 312.7 °C at 760 mmHg
• PKA: 14.77±0.20(Predicted)
• Flash Point: 177.8 °C
• PSA: 29.10000
• Density: 1.198 g/cm³
• LogP: 1.31920
• Storage Temp.: Refrigerator
• Solubility.: 9.1g/l
• Water Solubility.: insoluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Oxindole(2-Indolone) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1C2=CC=CC=C2NC1=O
• Uses: Indole analogue; shows pharmacological activity Oxindole is considered as indole analogue, which shows pharmacological activity.

Technology Process of Oxindole

There total 172 articles about Oxindole 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%

methyl (2-nitrophenyl)acetate (30095-98-8) → 2-oxoindole (59-48-3)

Guidance literature:

methyl (2-nitrophenyl)acetate; With hydrogen; In ethyl acetate; at 20 ℃; for 24h; under 7600.51 Torr; Autoclave;

In ethyl acetate; for 6h; Reflux; Molecular sieve;

DOI:10.1021/ol9001366

Reference yield: 98.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 2-oxoindole (59-48-3)

Guidance literature:

indole-2,3-dione; With hydrazine; In methanol; Heating;

With sodium ethanolate; In ethanol; Further stages.; Heating;

DOI:10.1021/ol016379r

Reference yield: 95.0%

2-(2-nitrophenyl)acetic acid (3740-52-1) → 2-oxoindole (59-48-3)

Guidance literature:

With iron; acetic acid; at 100 ℃;

DOI:10.1016/j.ejmech.2015.10.020

upstream raw materials:

tetrachloromethane

2'-chloro-benzeneacetic acid

dioxindol

spiro[[1,3]dithiolane-2,3'-indolin]-2'-one

Downstream raw materials:

3-(2-amino-benzylidene)-1,3-dihydro-indol-2-one

(3E)-3-(2-furylmethylidene)-1H-indol-2(3H)-one

indirubin

3-(3-oxo-3H-benzo[b]thiophen-2-ylidene)-1,3-dihydro-indol-2-one

Refernces

• 1、 Avula, Vijay Kumar Reddy,Chintha, Venkata Ramaiah,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju,Wudayagiri, Rajendra. "Synthesis, Docking, and Bioavailability of 2′-Oxo-3-phenylspiro[cyclopropane-1,3′-indoline]-2,2-dicarbonitriles as Antibacterial Agents In Silico". . p. 209 - 217. Retrieved 2019.
• 2、 Kungumathilagam,Karunakaran. "Kinetics and mechanism of meso-tetraphenylporphyriniron(III) chloride catalyzed oxidation of indole by peroxomonosulphate". . p. 4311 - 4314. Retrieved 2013.
• 3、 Meenakshisundaram, Subbiah,Sarathi. "Kinetics and mechanism of oxidation of indole by HSO5 -". . p. 46 - 51. Retrieved 2007.
• 4、 Mansour, Hany S.,Abd El-Wahab, Hend A. A.,Ali, Ahmed M.,Aboul-Fadl, Tarek. "Inversion kinetics of someE/Z3-(benzylidene)-2-oxo-indoline derivatives and theirin silicoCDK2 docking studies". . p. 7839 - 7850. Retrieved 2021/03/03.
• 5、 Huang, Tiao,Kong, Dulin,Li, Yue,Liu, Li,Wu, Mingshu. "A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids". . p. 2321 - 2328. Retrieved 2021/09/22.