4-Methylindole

Base Information

• Chemical Name: 4-Methylindole
• CAS No.: 16096-32-5
• Molecular Formula: C9H9N
• Molecular Weight: 131.177
• Hs Code.: 29339900
• European Community (EC) Number: 240-262-5
• UNII: 3338387XEA
• DSSTox Substance ID: DTXSID20167043
• Nikkaji Number: J236.662B
• Wikidata: Q27256216
• Mol file: 16096-32-5.mol

Synonyms:4-Methylindole;16096-32-5;4-Methyl-1H-indole;1H-Indole, 4-methyl-;4-methyl-indole;4-Methyindole;Indole, 4-methyl-;MFCD00005668;UNII-3338387XEA;EINECS 240-262-5;3338387XEA;4-methyl indole;SCHEMBL65514;SCHEMBL10266651;DTXSID20167043;BCP26932;BBL027536;STK503688;AKOS000265516;AB00476;AC-1392;CS-W001971;PS-3408;BP-10290;SY005776;AM20050546;FT-0602436;M1745;EN300-39431;M-3900;Q27256216;Z384970526

Chemical Property of 4-Methylindole

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid after melting
• Vapor Pressure: 0.0132mmHg at 25°C
• Melting Point: 5 °C
• Refractive Index: 1.606-1.608
• Boiling Point: 267.821 °C at 760 mmHg
• PKA: 17.36±0.30(Predicted)
• Flash Point: 114.058 °C
• PSA: 15.79000
• Density: 1.11 g/cm³
• LogP: 2.47630
• Storage Temp.: -20°C
• Sensitive.: Light Sensitive
• XLogP3: 2.4
• 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

4-Methylindole ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CNC2=CC=C1

Technology Process of 4-Methylindole

There total 53 articles about 4-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: 98.0%

1-(Methylsulfonyl)-4-methylindole (88131-65-1) → 4-methyl-1H-indole (16096-32-5,261352-49-2)

Guidance literature:

With potassium hydroxide; In methanol; for 18h; Heating;

DOI:10.1021/jo00176a007

Reference yield: 97.0%

4-methyl-2,3-dihydro-1H-indole (62108-16-1) → 4-methyl-1H-indole (16096-32-5,261352-49-2)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; chloropyridinecobaloxime(III); In ethanol; at 30 ℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation;

DOI:10.1002/anie.201612486

Reference yield: 90.0%

C26H39INO3Si(1+)*C7H7O3S(1-) → 4-methyl-1H-indole (16096-32-5,261352-49-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 4h; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.1c00820

upstream raw materials:

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

N-(2,3-dimethylphenyl)formamide

potassium ethoxide

4-formyl indole

Downstream raw materials:

4-methyl-1-tosyl-1H-indole

N-(3-nitrobenzene)sulfonyl-4-methylindole

C₁₈H₁₈N₂O₃

1-ethyl-4-methylindole

Refernces

• 1、 Ogura, Akihiro,Shibata, Kouhei,Takao, Ken-Ichi. "Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis". . p. 10067 - 10087. Retrieved 2021/07/26.
• 2、 Beaudry, Christopher M.,Points, Gary L.,Stout, Kenneth T.. "Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid". supporting information. p. 16655 - 16658. Retrieved 2020/12/01.