Ethanone, 2,2,2-trifluoro-1-(1H-indol-5-yl)- (9CI)

Base Information

• Chemical Name: Ethanone, 2,2,2-trifluoro-1-(1H-indol-5-yl)- (9CI)
• CAS No.: 170366-90-2
• Molecular Formula: C10H6 F3 N O
• Molecular Weight: 213.1559496
• Hs Code.: 2933998090
• Mol file: 170366-90-2.mol

Synonyms:5-Trifluoroacetylindole

Chemical Property of Ethanone, 2,2,2-trifluoro-1-(1H-indol-5-yl)- (9CI)

Chemical Property:

• Boiling Point: 308.6±37.0 °C(Predicted)
• PKA: 15.45±0.30(Predicted)
• PSA: 32.86000
• Density: 1.423±0.06 g/cm3(Predicted)
• LogP: 2.91290
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2,2,2-trifluoro-1-(1H-indol-5-yl)ethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethanone, 2,2,2-trifluoro-1-(1H-indol-5-yl)- (9CI)

There total 4 articles about Ethanone, 2,2,2-trifluoro-1-(1H-indol-5-yl)- (9CI) 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: 77.0%

5-bromo-1H-indole (10075-50-0) + N-(trifluoroacetyl)piperidine (340-07-8) → 2,2,2-trifluoro-1-(1H-indol-5-yl) ethan-1-one (170366-90-2)

Guidance literature:

5-bromo-1H-indole; With potassium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 1h; Inert atmosphere;

With tert.-butyl lithium; In tetrahydrofuran; mineral oil; pentane; at -78 ℃; for 0.25h; Inert atmosphere;

N-(trifluoroacetyl)piperidine; In tetrahydrofuran; mineral oil; pentane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo301552m

Reference yield: 72.0%

S-(tert-butyl)trifluorothioacetate (181820-18-8) + 1H-indole-5-boronic acid (144104-59-6) → 2,2,2-trifluoro-1-(1H-indol-5-yl) ethan-1-one (170366-90-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; In tetrahydrofuran; at 30 ℃; for 18h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.151780

Reference yield: 57.0%

5-bromo-1H-indole (10075-50-0) + trifluoroacetic acid (76-05-1) → 2,2,2-trifluoro-1-(1H-indol-5-yl) ethan-1-one (170366-90-2)

Guidance literature:

5-bromo-1H-indole; With tert.-butyl lithium; potassium hydride; In tetrahydrofuran; pentane; at -78 ℃; for 0.416667h;

trifluoroacetic acid; at -78 ℃; for 0.5h;

DOI:10.3987/COM-99-8480

upstream raw materials:

5-bromo-1H-indole

trifluoroacetic acid

trifluoroacetic anhydride

N-(trifluoroacetyl)piperidine

Downstream raw materials:

2,2,2-trifluoro-1-[1-di(4-fluorophenyl)methylindol-5-yl]-1-ethanone

Refernces

• 1、 Ban, Shu-Rong,Cao, Ya-Fang,Dai, Hui-Xiong,Wang, Xing,Xu, Hui,Yi, Xing. "Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature". supporting information. . Retrieved 2020/03/23.
• 2、 Takami, Hitoshi,Koshimura, Hirokazu,Kumazawa, Toshiaki. "Synthetic studies on trifluoroacetylindoles". . p. 1119 - 1124. Retrieved 2007/10/03.