2-Methylindole

Base Information

• Chemical Name: 2-Methylindole
• CAS No.: 95-20-5
• Molecular Formula: C9H9N
• Molecular Weight: 131.177
• Hs Code.: 2933.90
• European Community (EC) Number: 202-398-3
• NSC Number: 7514
• UNII: I7CN58827I
• DSSTox Substance ID: DTXSID5059117
• Nikkaji Number: J3.949G
• Wikipedia: 2-Methylindole
• Wikidata: Q4596907
• Metabolomics Workbench ID: 129884
• ChEMBL ID: CHEMBL259419
• Mol file: 95-20-5.mol

Synonyms:2-methylindole;2-methylindole sodium salt

Chemical Property of 2-Methylindole

Chemical Property:

• Appearance/Colour: yellow to reddish-purple or brown crystals, flakes
• Vapor Pressure: 0.0104mmHg at 25°C
• Melting Point: 57-59 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 272 °C at 760 mmHg
• PKA: 17.57±0.30(Predicted)
• Flash Point: 112.5 °C
• PSA: 15.79000
• Density: 1.11g/cm³
• LogP: 2.47630
• Storage Temp.: Freezer (-20°C)
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

2-Methylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-41
• Safety Statements: 36/37-24/25-39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: CC1=CC2=CC=CC=C2N1
• Uses: 2-Methylindole is an intermediate in the synthesis of indole derivative with potential antifungal activities. It can be used as a raw material for the preparation of deacetylase (HDAC) inhibitor panobinostat. 2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.

Technology Process of 2-Methylindole

There total 226 articles about 2-Methylindole 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: 96.0%

tert-butylethylene (558-37-2) + 2-methyl indoline (6872-06-6) → 2-methyl-1H-indole (95-20-5) + 2,2-Dimethylbutane (75-83-2)

Guidance literature:

With (PSCOP)IrHCl; sodium t-butanolate; In para-xylene; at 120 ℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;

DOI:10.1002/anie.201306559

Reference yield: 91.0%

2-methyl indoline (6872-06-6) → 2-methyl-1H-indole (95-20-5) + hydrogen (1333-74-0)

Guidance literature:

With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); potassium hexafluoroantimonate; 9-(2-mesityl)-10-methylacridinium perchlorate; In dichloromethane; at 20 ℃; for 45h; Irradiation; Inert atmosphere;

DOI:10.1021/jacs.7b00253

Reference yield: 90.0%

nitrobenzene (98-95-3,26969-40-4) + 2-methyl indoline (6872-06-6) → 2-methyl-1H-indole (95-20-5) + aniline (62-53-3)

Guidance literature:

With nickel-nitrogen-doped carbon framework; In water; at 145 ℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/c9gc04358f

upstream raw materials:

quinoline

3-Methylindole

3-acetyl-2-methylindole

2-methyl-1H-indole-3-carboxylic acid

Downstream raw materials:

2-methyl-3-indoleacetic acid

(2-methyl-1H-indol-3-yl)phenylmethanone

bis-(2-methyl-indol-3-yl)-phenyl-acetonitrile

2-methyl-3-[1,2-diphenyleth-1-enyl]-1H-indole

Refernces

• 1、 Yu, Ke,Liang, Yujie,Li, Bin,Wang, Baiquan. "Rhodium(III)-Catalyzed Synthesis of Indole Derivatives from Pyrimidyl-Substituted Anilines and Diazo Compounds". . p. 661 - 666. Retrieved 2016.
• 2、 Zamyshlyaeva, L. I.,Fomin, O. A.,Kvacheva, L. D.,Novikov, Yu. N.,Suvorov, N. N.. "FISCHER LIQUID - PHASE CYCLIZATION OF ARYLHYDRAZONES". . p. 1455 - 1458. Retrieved 1984.
• 3、 Takahashi et al.. "-". . p. 1725. Retrieved 1976.
• 4、 Hrutfiord,Bunnett. "-". . p. 4745. Retrieved 1958.
• 5、 Quan, Yangjian,Lan, Guangxu,Shi, Wenjie,Xu, Ziwan,Fan, Yingjie,You, Eric,Jiang, Xiaomin,Wang, Cheng,Lin, Wenbin. "Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis". supporting information. p. 3115 - 3120. Retrieved 2020/12/09.
• 6、 Huang, Lin,Bismuto, Alessandro,Rath, Simon A.,Trapp, Nils,Morandi, Bill. "Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism". supporting information. p. 7290 - 7296. Retrieved 2021/03/01.