1-Methylindole

Base Information

• Chemical Name: 1-Methylindole
• CAS No.: 603-76-9
• Molecular Formula: C9H9N
• Molecular Weight: 131.177
• Hs Code.: 29339990
• European Community (EC) Number: 210-057-5
• NSC Number: 212534
• UNII: 8H698ROJ5F
• DSSTox Substance ID: DTXSID3060534
• Nikkaji Number: J45.593H
• Wikipedia: 1-Methylindole
• Wikidata: Q4545796
• ChEMBL ID: CHEMBL19912
• Mol file: 603-76-9.mol

Synonyms:1-methylindole;1-methylindole monopicrate

Chemical Property of 1-Methylindole

Chemical Property:

• Appearance/Colour: deep yellow viscous liquid with a very unpleasant smell
• Vapor Pressure: 0.0622mmHg at 25°C
• Melting Point: 94 - 95oC
• Refractive Index: n20/D 1.606(lit.)
• Boiling Point: 239.377 °C at 760 mmHg
• Flash Point: 98.572 °C
• PSA: 4.93000
• Density: 1.008 g/cm³
• LogP: 2.17830
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Light Sensitive
• Water Solubility.: insoluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• 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

1-Methylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: CN1C=CC2=CC=CC=C21
• General Description: 1-Methylindole (N-methylindole) is an indole derivative that exhibits regioselective reactivity in palladation reactions, where the choice of reaction conditions (e.g., base, acid, and protective groups) influences the formation of either C2-Pd or C3-Pd bonds. The study highlights its role in forming tetranuclear palladacycles, demonstrating how N-substitution and reaction medium acidity can dictate the selectivity of metalation at specific positions on the indole ring.

Technology Process of 1-Methylindole

There total 166 articles about 1-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: 99.0%

indole (120-72-9) + methyl iodide (74-88-4) → 1-methylindole (603-76-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/ol060039u

Reference yield: 99.0%

indole (120-72-9) → 1-methylindole (603-76-9)

Guidance literature:

indole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere; Sealed tube;

methyl halide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b03243

Reference yield: 99.0%

N-methylindoline (824-21-5) → 1-methylindole (603-76-9)

Guidance literature:

With H₈O₂₀P₈Pt₂^(4-)*4C₃₄H₇₂N⁽¹⁺⁾; In methanol; Inert atmosphere; Irradiation;

DOI:10.1039/c8sc05600e

upstream raw materials:

1,2-dimethyl-4,5-dihydropyrrole

indole

Dimethyl ether

dimethyl sulfate

Downstream raw materials:

1-methyl-3-(1-piperidylmethyl)-indole

ZIN⁽⁷⁶⁸⁾C₀₁₃₄₄

2-(1-methyl-1H-indol-3-yl)acetic acid

ethyl 2-(1-methyl-1H-indol-3-yl)acetate

Refernces

Mechanistic insight into the regioselective palladation of indole derivatives: Tetranuclear indolyl palladacycles with high C2-Pd or C3-Pd bond selectivity

10.1021/om300284t

The research focuses on the regioselective palladation of indole derivatives, aiming to understand the factors influencing the selectivity of C2?Pd or C3?Pd bond formation. The experiments involved the palladation of N-phenylindole (1a) and N-methylindole (1b) under different reaction conditions to capture both C2?Pd and C3?Pd intermediates. Key reactants included [Pd(OAc)2] (2a) as the palladium source, sodium pivalate (PivONa) as a base for C3 palladation, and PivOH with NaCl for C2 palladation. The experiments were designed to investigate the effect of N-substituted protective groups and the acidity of the reaction medium on the regioselectivity. Analytical techniques used included X-ray crystallography for structural characterization of the synthesized tetranuclear indolyl palladacycles, which provided insights into the regioselective palladation mechanism and the influence of reaction conditions on the C2?Pd or C3?Pd bond selectivity.

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