5-Chlorooxindole

Base Information

• Chemical Name: 5-Chlorooxindole
• CAS No.: 17630-75-0
• Molecular Formula: C8H6ClNO
• Molecular Weight: 167.595
• Hs Code.: 2933.99
• European Community (EC) Number: 412-200-9,623-924-1
• DSSTox Substance ID: DTXSID6057667
• Nikkaji Number: J416.474A
• Wikidata: Q72456272
• ChEMBL ID: CHEMBL2381491
• Mol file: 17630-75-0.mol

Synonyms:2H-Indol-2-one, 5-chloro-1,3-dihydro-;5-Chlor-1,3-dihydro-2H-indol-2-on;5-chloroindolin-2-one;

Chemical Property of 5-Chlorooxindole

Chemical Property:

• Appearance/Colour: Tan powder
• Vapor Pressure: 0.00881mmHg at 25°C
• Melting Point: 194-197 °C(lit.)
• Refractive Index: 1.663
• Boiling Point: 348.3 °C at 760 mmHg
• PKA: 13.14±0.20(Predicted)
• Flash Point: 164.5 °C
• PSA: 29.10000
• Density: 1.362 g/cm³
• LogP: 1.97260
• Storage Temp.: Keep Cold
• Solubility.: Slightly Soluble (2.0 g/L) (25°C).
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 167.0137915
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-2-oxindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-43-52/53-62-36/37/38
• Safety Statements: 22-36/37-61-45-36/37/39-24-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)Cl)NC1=O
• Uses: 5-Chlorooxindole is used in the preparation of novel GSK-3β inhibitors as anticancer agents. 5-Chloro-2-oxindole was used for the quantitation of 5-chloro-2-oxindole, concomitantly with all of its potential positional isomers using a single, highly specific, normal-phase chromatographic system. 5-Chloro-2-oxindole (5-Chlorooxindole) is a starting material for tenidap sodium, a pharmaceutical drug candidate. 5-Chloro-2-oxindole was used for the quantitation of 5-chloro-2-oxindole, concomitantly with all of its potential positional isomers using a single, highly specific, normal-phase chromatographic system.

Technology Process of 5-Chlorooxindole

There total 47 articles about 5-Chlorooxindole 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: 100.0%

5-chloro-2-oxo-2,3-dihydro-indole-1,3-dicarboxylic acid dibenzyl ester → 5-chloro-indolin-2-one (17630-75-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jm701383e

Reference yield: 90.0%

5-chloroindole 2,3-dione (17630-76-1) → 5-chloro-indolin-2-one (17630-75-0)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.02.072

Reference yield: 90.0%

N-(4-chlorophenyl)acetamide (539-03-7) + ethyl iodoacetae (623-48-3) → 5-chloro-indolin-2-one (17630-75-0)

Guidance literature:

With silver(I) acetate; palladium diacetate; trifluoroacetic acid; at 120 ℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0035-1561856

upstream raw materials:

1-methoxyindolin-2-one

2-chloro-N-(4-chlorophenyl)acetamide

3,3-Dibromo-5-chloroindol-2(3H)-one

(5-chloro-2-nitro-phenyl)acetic acid methyl ester

Downstream raw materials:

5-chloro-3-(3,4-dichlorobenzylidene)-oxindole

5-chlorooindoline-2-thione

5-chloro-1-{3-[4-(3-chlorophenyl)-1-piperazinyl]propyl}indolin-2-one

5-chloro-1-ethoxycarbonyl-2-(ethoxycarbonyloxy)indole

Refernces

• 1、 Zhang, Chao,Xu, Juan,Zhao, Xinyu,Kang, Congmin. "Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones". . p. 537 - 540. Retrieved 2017.
• 2、 Dandia,Bhati,Jain,Sharma. "Ultrasound promoted clay catalyzed efficient and one pot synthesis of substituted oxindoles". . p. 1143 - 1147. Retrieved 2011.
• 3、 Liu, Li,Li, Yue,Huang, Tiao,Kong, Dulin,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.
• 4、 Jiang, Xinpeng,Zheng, Cong,Lei, Lijun,Lin, Kai,Yu, Chuanming. "Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation". . p. 1437 - 1442. Retrieved 2018/04/06.