4-Ethenyl-1H-indole

Base Information

• Chemical Name: 4-Ethenyl-1H-indole
• CAS No.: 68900-05-0
• Molecular Formula: C10H9N
• Molecular Weight: 143.188
• Mol file: 68900-05-0.mol

Synonyms:

Chemical Property of 4-Ethenyl-1H-indole

Chemical Property:

• PSA: 15.79000
• LogP: 2.81090

Purity/Quality:

4-ethenyl-1H-Indole 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Ethenyl-1H-indole

There total 10 articles about 4-Ethenyl-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: 75.0%

4-formyl indole (1074-86-8) + Methyltriphenylphosphonium bromide (1779-49-3) → 4-vinylindole (68900-05-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 2h; Inert atmosphere;

4-formyl indole; In tetrahydrofuran; hexane; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jacs.0c08532

Reference yield: 34.0%

4-bromo-1H-indole (52488-36-5) + pinacol vinylboronate (75927-49-0) → 4-vinylindole (68900-05-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; water; toluene; at 80 ℃; Inert atmosphere;

DOI:10.1002/anie.201801525

Reference yield:

2-methyl-3-nitro-benzoic acid methyl ester (59382-59-1) → 4-vinylindole (68900-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / dimethylformamide / 6 h / 130 °C

2: 82 percent / hydrogen / 10percent Pd/C / benzene / 1.5 h / 2585.7 Torr

3: 97 percent / diisobutylaluminium hydride / diethyl ether; toluene / -70 °C

4: 90.4 percent / active manganese dioxide / CH₂Cl₂ / 48 h / Ambient temperature

5: 1) n-BuLi / 1) THF, 30 min room temperature 2) THF, 1h below 30 deg C

With manganese(IV) oxide; n-butyllithium; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo01304a043

upstream raw materials:

4-formyl indole

Methyltriphenylphosphonium bromide

Methylenetriphenylphosphorane

1-(tert-butyldimethylsiloxy)-2-propanone

Refernces

• 1、 Winn, Michael,Francis, Daniel,Micklefield, Jason. "De novo Biosynthesis of “Non-Natural” Thaxtomin Phytotoxins". supporting information. p. 6830 - 6833. Retrieved 2018/06/04.
• 2、 Kozikowski,Ishida,Chen. "New synthesis and some selected reactions of the potential ergot alkaloid precursor indole-4-carboxaldehyde". . p. 3350 - 3352. Retrieved 2007/10/02.