3-Methyloxindole

Base Information

• Chemical Name: 3-Methyloxindole
• CAS No.: 1504-06-9
• Molecular Formula: C9H9 N O
• Molecular Weight: 147.177
• Hs Code.: 2933790090
• UNII: M6O509COF9
• DSSTox Substance ID: DTXSID30933933
• Nikkaji Number: J70.978F
• Wikidata: Q74416961
• Metabolomics Workbench ID: 50897
• Mol file: 1504-06-9.mol

Synonyms:3-methyl-2-oxindole;3-methyloxindole

Chemical Property of 3-Methyloxindole

Chemical Property:

• Vapor Pressure: 0.00405mmHg at 25°C
• Melting Point: 117-121 °C(lit.)
• Boiling Point: 279.3°Cat760mmHg
• PKA: 14.81±0.40(Predicted)
• Flash Point: 157.9°C
• PSA: 29.10000
• Density: 1.123g/cm³
• LogP: 1.88020
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• 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

3-Methyloxindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C2=CC=CC=C2NC1=O
• Uses: 3-Methylindole metabolite. ? ;Reactant for enantioselective α-amination reactions1? ;Reactant for aldol reaction with glyoxal derivatives2? ;Reactant for amine thiourea catalyzed conjugate addition to α,β-unsaturated aldehydes3? ;Reactant for O-acetylation reactions4? ;Reactant for preparation of a disubstituted oxoindole by using rhodium-catalyzed cyclopropanation/ring-opening reactions5 A versatile reactant. As 3-Methylindole metabolite. Reactant for enantioselective α-amination reactions, Reactant for aldol reaction with glyoxal derivatives, Reactant for amine thiourea catalyzed conjugate addition to α,β-unsaturated aldehydes, Reactant for O-acetylation reactions, Reactant for preparation of a disubstituted oxoindole by using rhodium-catalyzed cyclopropanation/ring-opening reactions.

Technology Process of 3-Methyloxindole

There total 87 articles about 3-Methyloxindole 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%

3-Methylindole (83-34-1) → 3-methylindolin-2-one (1504-06-9)

Guidance literature:

With hydrogenchloride; dimethyl sulfoxide; at 20 ℃;

DOI:10.1021/acs.joc.1c02435

Reference yield: 100.0%

N-hydroxyl-3-methylindolin-2-one (131387-95-6) → 3-methylindolin-2-one (1504-06-9)

Guidance literature:

With carbon monoxide; boric acid; triphenylphosphine; palladium dichloride; In tetrahydrofuran; at 80 ℃; for 20h; under 26601.8 Torr;

DOI:10.1021/acscatal.8b02863

Reference yield: 95.0%

carbon monoxide (201230-82-2) + 2-vinylaniline (3867-18-3) → 3-methylindolin-2-one (1504-06-9)

Guidance literature:

With palladium diacetate; hydrogen; tricyclohexylphosphine; In dichloromethane; at 100 ℃; for 48h; under 31028.9 Torr;

DOI:10.1021/ja953403l

upstream raw materials:

3-Methylindole

2-oxoindole

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

3-Acetylindol-2-one

Downstream raw materials:

3-hydroxy-3-methyloxindole

2-aminoacetophenone

(R,S)-2-Aminophenylpropionic acid

α-(3-benzylphenyl)-propionic acid

Refernces

• 1、 Rodriguez, J. Gonzalo,Canoira, Laureano,Temprano, Fernando. "Cyclization of N-Alkenyl-o-chloroanilides with Organonickel(0) Complexes: Conformational Analysis of 3-Substituted Oxindoles". . p. 1193 - 1196. Retrieved 1986.
• 2、 Baudoux, Jér?me,Salit, Anne-Frédérique,Cahard, Dominique,Plaquevent, Jean-Christophe. "Ionic liquids as solvents of choice for electrophilic fluorination: Fluorination of indoles by F-TEDA-BF4". . p. 6573 - 6574. Retrieved 2002.
• 3、 Takeuchi, Yoshio,Tarui, Takanao,Shibata, Norio. "A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by selectfluor". . p. 639 - 642. Retrieved 2000.
• 4、 Herth, Matthias M.,Andersen, Valdemar L.,Hansen, Hanne D.,Stroth, Nikolas,Volk, Balázs,Lehel, Szabolcs,Dyssegaard, Agnete,Ettrup, Anders,Svenningsson, Per,Knudsen, Gitte M.,Kristensen, Jesper L.. "Evaluation of 3-ethyl-3-(phenylpiperazinylbutyl)oxindoles as PET ligands for the serotonin 5-HT7 receptor: Synthesis, pharmacology, radiolabeling, and in vivo brain imaging in pigs". . p. 3631 - 3636. Retrieved 2015.
• 5、 Mintz, Tomer,More, Nagnath Yadav,Gaster, Eden,Pappo, Doron. "Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles". supporting information. p. 18164 - 18178. Retrieved 2021/12/17.
• 6、 Zhao, Guodong,Liang, Lixin,Wang, Eryu,Lou, Shaoyan,Qi, Rui,Tong, Rongbiao. "Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide". supporting information. p. 2300 - 2307. Retrieved 2021/04/12.