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:

98% ^*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
• Uses: 1-Methylindole is useful for the determination of association constant for the electron-donor-acceptor complexes with 1-(2,4,6-trinitrophenyl) propan-2-one. It acts as a reactant for the preparation of polycyclic derivatives of indoles, bisindole derivatives and pharmaceutically active 2-oxo-1-pyrrolidine analogues. It is also used as a reactant for the preparation of Positron Emission Tomography (PET) imaging agents of protein kinase C (PKC) and glycogen synthase kinase-3 (GSK-3).

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

• 1、 Reinecke et al.. "-". . p. 3066. Retrieved 1972.
• 2、 Maruoka,Oishi,Yamamoto. "Regioselective Fischer indole synthesis mediated by organoaluminum amides". . p. 7638 - 7639. Retrieved 1993.
• 3、 Jorapur, Yogesh R.,Jeong, Jae Min,Chi, Dae Yoon. "Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids". . p. 2435 - 2438. Retrieved 2006.
• 4、 Zhang, Shang-Shi,Liu, Yan-Zhi,Zheng, Yi-Chuan,Xie, Hui,Chen, Shao-Yong,Song, Jia-Lin,Shu, Bing. "Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position". supporting information. p. 64 - 70. Retrieved 2021/11/03.
• 5、 Chelvam, Venkatesh,Dudhe, Premansh,Krishnan, Mena Asha,Pathak, Biswarup,Roy, Diptendu,Venkatasubbaiah, Krishnan,Yadav, Kratika. "Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation". supporting information. p. 1453 - 1463. Retrieved 2021/07/02.