5-Benzyl-1H-indole

Base Information

• Chemical Name: 5-Benzyl-1H-indole
• CAS No.: 23543-62-6
• Molecular Formula: C15H13N
• Molecular Weight: 207.27
• Hs Code.: 2933990090
• Mol file: 23543-62-6.mol

Synonyms:5-Benzyl-1H-indole

Chemical Property of 5-Benzyl-1H-indole

Chemical Property:

• Boiling Point: 382.2±11.0 °C(Predicted)
• PKA: 17.20±0.30(Predicted)
• PSA: 15.79000
• Density: 1.143±0.06 g/cm3(Predicted)
• LogP: 3.75870

Purity/Quality:

5-BENZYL-1H-INDOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Benzyl-1H-indole

There total 12 articles about 5-Benzyl-1H-indole 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%

benzyl chloride (100-44-7) + 1H-indole-5-boronic acid (144104-59-6) → 5-benzyl-1H-indole (23543-62-6)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-dimethyl-3-(2-phenoxyphenyl)-1-(2,4,6-trimethylbenzyl)imidazolium chloride; water; caesium carbonate; In 1,4-dioxane; at 90 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jo5009178

Reference yield: 79.0%

5-bromo-1H-indole (10075-50-0) + iodomethylbenzene (620-05-3) → 5-benzyl-1H-indole (23543-62-6)

Guidance literature:

With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); zinc; In N,N-dimethyl-formamide; at 37 ℃; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/chem.202103353

Reference yield: 60.0%

5-methoxylindole (1006-94-6) + phenylmagnesium bromide (1589-82-8) → 5-benzyl-1H-indole (23543-62-6)

Guidance literature:

With nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; In tetrahydrofuran; toluene; at 100 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.5b02200

upstream raw materials:

5-benzyl-indole-2-carboxylic acid

p-benzylaniline

ethyl 5-benzyl-1H-indole-2-carboxylate

benzyl chloride

Downstream raw materials:

5-benzylindole-3-carboxaldehyde

Refernces

• 1、 Tobisu, Mamoru,Takahira, Tsuyoshi,Chatani, Naoto. "Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage". supporting information. p. 4352 - 4355. Retrieved 2015/09/15.
• 2、 Tellis, John C.,Primer, David N.,Molander, Gary A.. "Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis". . p. 433 - 436. Retrieved 2014/08/05.