2-(trifluoromethyl)-1H-indole

Base Information

• Chemical Name: 2-(trifluoromethyl)-1H-indole
• CAS No.: 51310-54-4
• Molecular Formula: C9H6F3N
• Molecular Weight: 185.149
• Hs Code.: 2933990090
• European Community (EC) Number: 803-765-6
• DSSTox Substance ID: DTXSID60448762
• Nikkaji Number: J703.441E
• Wikidata: Q72512034
• Mol file: 51310-54-4.mol

Synonyms:2-(trifluoromethyl)-1H-indole;51310-54-4;2-TRIFLUOROMETHYLINDOLE;2-Trifluoromethyl-1H-indole;1H-Indole, 2-(trifluoromethyl)-;MFCD04972104;2-(Trifluoromethyl)indole;SCHEMBL30145;2-trifluoromethyl-(1H)-indole;2-(trifluoromethyl)-1 H-Indole;DTXSID60448762;2-(Trifluoromethyl)indole, 97%;BBL103694;STL557504;AKOS005256037;CS-W016961;AC-22694;DS-14011;FT-0681653;EN300-245533;T-6385;A871313

Chemical Property of 2-(trifluoromethyl)-1H-indole

Chemical Property:

• Vapor Pressure: 0.024mmHg at 25°C
• Melting Point: 106-110°C
• Refractive Index: 1.556
• Boiling Point: 256.676 °C at 760 mmHg
• PKA: 14.62±0.30(Predicted)
• Flash Point: 109.034 °C
• PSA: 15.79000
• Density: 1.368 g/cm³
• LogP: 3.18670
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 185.04523368
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

2-(trifluoromethyl)-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)C(F)(F)F

Technology Process of 2-(trifluoromethyl)-1H-indole

There total 11 articles about 2-(trifluoromethyl)-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: 48.0%

(Z)-2,2,2-trifluoro-N-(o-tolyl)acetimidoyl chloride + cesium acetate (3396-11-0) → 2-(trifluoromethyl)indole (51310-54-4) + N-acetyl-N-(o-tolyl)acetamide (3026-99-1)

Guidance literature:

With bis(dibenzylideneacetone)-palladium⁽⁰⁾; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene; In toluene; at 110 ℃; for 12h; Reagent/catalyst; Glovebox; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00795

Reference yield: 32.0%

indole (120-72-9) + 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate (1961266-44-3) → 2-(trifluoromethyl)indole (51310-54-4) + 3-(trifluoromethyl)-1H-indole (51310-55-5)

Guidance literature:

With [(Tp)Ni^IV(CF₃)₃]; In dimethyl sulfoxide; at 25 ℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1021/jacs.9b06383

Reference yield: 18.0%

indole (120-72-9) + difluorodiiodomethane (1184-76-5) → 2-(trifluoromethyl)indole (51310-54-4) + 3-(trifluoromethyl)-1H-indole (51310-55-5)

Guidance literature:

In N,N-dimethyl-formamide; for 30h; Irradiation;

upstream raw materials:

indole

difluorodiiodomethane

bis(trifluoroacetyl)peroxide

trimethylsilyl indole

Downstream raw materials:

2-trifluoromethyl-indole-3-acetic acid

N-benzyl-2-[2-(trifluoromethyl)-1H-indol-1-yl]-5,6,7,8-tetrahydroquinazolin-4-amine

(E)-3-(4-(2-hydroxyethoxy)-3,5-dimethoxyphenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide

(E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide

Refernces

• 1、 Meucci, Elizabeth A.,Nguyen, Shay N.,Camasso, Nicole M.,Chong, Eugene,Ariafard, Alireza,Canty, Allan J.,Sanford, Melanie S.. "Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes". supporting information. p. 12872 - 12879. Retrieved 2019/08/26.
• 2、 Miller, Shelli A.,van Beek, Bas,Hamlin, Trevor A.,Bickelhaupt, F. Matthias,Leadbeater, Nicholas E.. "A methodology for the photocatalyzed radical trifluoromethylation of indoles: A combined experimental and computational study". supporting information. p. 94 - 100. Retrieved 2018/08/28.