1-Methyl-2-indolinone

Base Information

• Chemical Name: 1-Methyl-2-indolinone
• CAS No.: 61-70-1
• Molecular Formula: C9H9 N O
• Molecular Weight: 147.177
• Hs Code.: 2933790090
• European Community (EC) Number: 612-193-4
• NSC Number: 97219
• UNII: BKN6HNS2AW
• DSSTox Substance ID: DTXSID60209850
• Nikkaji Number: J103.209G
• Wikidata: Q83084324
• ChEMBL ID: CHEMBL41326
• Mol file: 61-70-1.mol

Synonyms:61-70-1;1-methylindolin-2-one;1-Methyl-2-indolinone;1-Methyl-2-oxindole;1-Methyloxindole;N-Methyloxindole;N-Methyl-2-indolinone;2-INDOLINONE, 1-METHYL-;N-Methylindol-2(3H)-one;1-methyl-3H-indol-2-one;1-Methylindol-2(3H)-one;1-Methyl-1,3-dihydro-2H-indol-2-one;Oxindole, 1-methyl-;2H-Indol-2-one, 1,3-dihydro-1-methyl-;BA 2777;1,3-Dihydro-1-methyl-2H-indol-2-one;NSC 97219;1-methyl-2,3-dihydro-1H-indol-2-one;1-Methyl-2-indolone;1-Methyl-1,3-dihydroindol-2-one;BKN6HNS2AW;1-Methyl-1,3-dihydro-indol-2-one;BRN 0124173;2H-Indol-2-one,1,3-dihydro-1-methyl-;NSC97219;MFCD00030253;NSC-97219;1-Methyl-2-oxindole (1-Methyl-2-indolone);5-21-08-00008 (Beilstein Handbook Reference);N-Methyl-2-oxindole;2,3-Dihydro-1-methylindol-2-one;N-methylindolin-2-one;UNII-BKN6HNS2AW;CHEMBL41326;SCHEMBL578262;1-Methyl-2-oxindole, 97%;Oxindole, 1-methyl- (6CI);RSQUAQMIGSMNNE-UHFFFAOYSA-;DTXSID60209850;methyl-1,3-dihydro-indol-2-one;HMS1578E04;1-METHYL-1H-INDOLIN-2-ONE;STL260057;AKOS000359704;2H-Indol-2-one,3-dihydro-1-methyl-;BA-2777;CS-W013308;SB66124;AC-14400;CS-10396;LS-83565;SY042826;TS-01920;1-Methyl-1,3-dihydro-2H-indol-2-one #;A8547;AM20040846;FT-0631274;EN300-17172;Z56899025

Chemical Property of 1-Methyl-2-indolinone

Chemical Property:

• Vapor Pressure: 5.92E-05mmHg at 25°C
• Melting Point: 85-88 °C(lit.)
• Boiling Point: 346oC at 760 mmHg
• PKA: 0.40±0.20(Predicted)
• Flash Point: 172.3oC
• PSA: 20.31000
• Density: 1.167g/cm3
• LogP: 1.27050
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 178

Purity/Quality:

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

1-Methyl-2-oxindole(1-Methyl-2-indolone) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)CC2=CC=CC=C21
• Uses: 1-Methyl-2-indolone is a reactant for preparation of fluorescent analogues of strigolactones as affectors of parasitic weed germination and fungal branching, irreversible Nek2 Kinase Inhibitors and anticancer agents. Reactant for preparation of:Fluorescent analogues of strigolactones as affectors of parasitic weed germination and fungal branchingIrreversible Nek2 Kinase InhibitorsAnticancer agentsAntimalarial agentsAntitimor agentsGermination stimulants in plantsInducers of NAD(P)H-quinone oxidoreductase 1 (NQO1)Retinoic acid analogsPotential anti-multiple sclerosis agentsInhibitors of human immunodeficiency virus type 1 (HIV-1) integrase 1-Methyl-2-oxindole is used in the prevention and therapy of atherosclerotic degradation of arterial walls.

Technology Process of 1-Methyl-2-indolinone

There total 12 articles about 1-Methyl-2-indolinone 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: 76.0%

1-methyl-1H-indole-2,3-dione (2058-74-4) → N-methyl-2-indolinone (61-70-1) + acetone (67-64-1)

Guidance literature:

With isopropyl alcohol; at 15 ℃; for 10h; Irradiation;

DOI:10.3987/COM-95-7272

Reference yield: 51.0%

2-(octan-2-yloxy)-1-methylindole → N-methyl-2-indolinone (61-70-1) + rac-octan-2-ol (4128-31-8,113301-48-7,4128-32-9)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; water; at 20 ℃; for 10h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.0c02506

Reference yield: 51.0%

acetic acid-(2-chloro-N-methyl-anilide) (74585-34-5) → N-methyl-2-indolinone (61-70-1) + 2-(N-acetyl-N-methylamino)phenol (573-27-3)

Guidance literature:

With potassium amide; In ammonia; benzene; for 0.5h; Irradiation;

DOI:10.1021/ja00288a027

upstream raw materials:

1-methylindole

phenylhydroxamoyl chloride

acetic acid-(2-chloro-N-methyl-anilide)

tetramethylviolacein

Downstream raw materials:

(1-methyl-2-oxo-indoline-3,3-diyl)-di-acetic acid diethyl ester

3-(4-diethylamino-phenylimino)-1-methyl-indolin-2-one

(E)-1-methyl-[3,3'-biindolinylidene]-2,2'-dione

(E)-1-methyl-3-benzylidene-2,3-dihydro-1H-indol-2-one

Refernces

• 1、 Paris, Timothy J.,Schwartz, Chris,Willand-Charnley, Rachel. "Electrophilic Etherification of α-Heteroaryl Carbanions with Monoperoxyacetals as a Route to Ketene O, O- And N, O-Acetals". . p. 2369 - 2384. Retrieved 2021/02/06.
• 2、 Shaughnessy, Kevin H.,Hamann, Blake C.,Hartwig, John F.. "Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles". . p. 6546 - 6553. Retrieved 2007/10/03.