5-Chloroacetyl-6-chlorooxindole

Base Information

• Chemical Name: 5-Chloroacetyl-6-chlorooxindole
• CAS No.: 118307-04-3
• Molecular Formula: C10H7Cl2NO2
• Molecular Weight: 244.077
• Hs Code.: 29147000
• DSSTox Substance ID: DTXSID60395646
• Nikkaji Number: J3.189.806D
• Wikidata: Q72516875
• Mol file: 118307-04-3.mol

Synonyms:118307-04-3;5-chloroacetyl-6-chlorooxindole;6-chloro-5-(2-chloroacetyl)indolin-2-one;6-chloro-5-(2-chloroacetyl)-1,3-dihydroindol-2-one;6-chloro-5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one;5-CHLOROACETYL-6-CHLORO-1,3-DIHYDROINDOL-2H-INDONE-2-ONE;5-Chloroacetyl-6-chloro-1,3-dihydro-2H-indole-2-one;2H-Indol-2-one, 6-chloro-5-(chloroacetyl)-1,3-dihydro-;6-chloro-5-(2-chloro-acetyl)-1,3-dihydro-indol-2-one;SCHEMBL622063;5-Cloroacetyl-6-chlorooxindole;6-Chloro-5-(chloro acetyl)-1-,3-dihydro-2H-indol-2-one;DTXSID60395646;LWWVMDRRHHCTMZ-UHFFFAOYSA-N;BCP19226;BBL010823;MFCD04115735;STK628800;5-(2-chloroacetyl)-6-chlorooxindole;AKOS005561611;AB20497;5-(2-Chloro acetyl)-6-chloro oxindole;5-(2-Chloro acetyl) -6-chloro oxindole;AC-23359;VS-02698;CS-0054239;FT-0642888;5-(2-CHLOROACETYL)-6-CHLORO-2-OXINDOLE;A803907;J-003735;J-518578;5-(1-Oxo-2-chloroethyl)-6-chloro-1H-indole-2(3H)-one;6-CHLORO-5-(2-CHLOROACETYL)-2,3-DIHYDRO-1H-INDOL-2-ONE;6-Chloro-5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one, AldrichCPR

Chemical Property of 5-Chloroacetyl-6-chlorooxindole

Chemical Property:

• Appearance/Colour: Light brown solid
• Vapor Pressure: 6.54E-08mmHg at 25°C
• Melting Point: 202-206 °C
• Refractive Index: 1.603
• Boiling Point: 430.1 °C at 760 mmHg
• PKA: 12.55±0.20(Predicted)
• Flash Point: 213.9 °C
• PSA: 46.17000
• Density: 1.471 g/cm³
• LogP: 2.39410
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 242.9853839
• Heavy Atom Count: 15
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

5-Chloroacetyl-6-chloro-1,3-dihydroindol-2H-indone-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 34
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC(=C(C=C2NC1=O)Cl)C(=O)CCl
• Uses: 5-Chloroacetyl-6-chloro-1,3-dihydroindol-2H-indone-2-one (cas# 118307-04-3) is a compound useful in organic synthesis.

Technology Process of 5-Chloroacetyl-6-chlorooxindole

There total 5 articles about 5-Chloroacetyl-6-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: 90.6%

6-chloro-2-oxindole (56341-37-8) + chloroacetyl chloride (79-04-9) → 6-chloro-5-(2-chloroacetyl) indolin-2-one (118307-04-3)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 0 - 30 ℃; for 24h; Inert atmosphere;

Reference yield:

chloroacetyl chloride (79-04-9) → 6-chloro-5-(2-chloroacetyl) indolin-2-one (118307-04-3)

Guidance literature:

6-chloro-2-oxindole; aluminum (III) chloride; In dichloromethane; at 4 - 26 ℃; for 0.5h;

chloroacetyl chloride; In dichloromethane; for 9h; Heating / reflux;

With hydrogenchloride; water; In dichloromethane; at 0 ℃; for 0.75h;

Reference yield:

2,5-dichloronitrobenzene (89-61-2) → 6-chloro-5-(2-chloroacetyl) indolin-2-one (118307-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / dimethyl sulfoxide / 25 - 30 °C / Inert atmosphere

1.2: 16 h / 40 - 85 °C

2.1: hydrogenchloride; tin / water; methanol / 10 - 70 °C

3.1: aluminum (III) chloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

3.2: 35 - 37 °C / Inert atmosphere

With hydrogenchloride; aluminum (III) chloride; tin; potassium carbonate; In methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane;

upstream raw materials:

6-chloro-2-oxindole

chloroacetyl chloride

2,5-dichloronitrobenzene

dimethyl (4-chloro-2-nitrophenyl)malonate

Downstream raw materials:

6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid

6-chloro-5-(2-chloroethyl)-2-oxindole

6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one

5-(2-(4-(1,2-benzisothiazole-3-yl)-1-piperazinyl)-1-oxoethyl)-6-chloro-1,3-dihydro-2H-indole-2-one

Refernces

• 1、 Guo, Jing,Zhu, Mingyue,Wu, Tianxiao,Hao, Chenzhou,Wang, Kai,Yan, Zizheng,Huang, Wanxu,Wang, Jian,Zhao, Dongmei,Cheng, Maosheng. "Discovery of indolin-2-one derivatives as potent PAK4 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study". . p. 3500 - 3511. Retrieved 2017/05/29.
• 2、 Nadkarni, Durgesh V.,Hallissey, James F.. "Improved process for the preparation of 6-chloro-5-(2-chloroethyl)oxindole". supporting information. p. 1142 - 1145. Retrieved 2013/01/03.