5-(Trifluoromethyl)indole

Base Information

• Chemical Name: 5-(Trifluoromethyl)indole
• CAS No.: 100846-24-0
• Molecular Formula: C9H6F3N
• Molecular Weight: 185.149
• Hs Code.: 2933990090
• European Community (EC) Number: 634-474-0
• DSSTox Substance ID: DTXSID30376720
• Nikkaji Number: J1.198.319G
• Wikidata: Q72512037
• Mol file: 100846-24-0.mol

Synonyms:5-(TRIFLUOROMETHYL)INDOLE;100846-24-0;5-(trifluoromethyl)-1H-indole;5-Trifluoromethylindole;1H-Indole, 5-(trifluoromethyl)-;5-trifluoromethyl indole;5-Trifluoromethyl-1H-indole;MFCD03095341;SCHEMBL438997;DTXSID30376720;5-(Trifluoromethyl)indole, 97%;AMY14429;BBL100428;STL554222;AKOS005254605;CS-W008231;FS-3578;SB15232;SY031828;FT-0601320;EN300-43994;A800281;J-000232;J-516447;Z445172364

Chemical Property of 5-(Trifluoromethyl)indole

Chemical Property:

• Appearance/Colour: Beige powder
• Vapor Pressure: 0.000105mmHg at 25°C
• Melting Point: 67-69 °C
• Refractive Index: 1.589
• Boiling Point: 256.7 °C at 760 mmHg
• PKA: 15.94±0.30(Predicted)
• Flash Point: 109 °C
• PSA: 15.79000
• Density: 1.367 g/cm³
• LogP: 3.18670
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• XLogP3: 3.2
• 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:

98%,99%, ^*data from raw suppliers

5-(Trifluoromethyl)indole ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1C(F)(F)F
• Uses: In 3-Naphthylindole construction by rhodium (II)-catalyzed regioselective direct arylation of indoles with 1-diazonaphthalen-2-(1H)-ones treatment of 5-(trifluoromethyl)indole(1k) or 6-(trifluoromethyl)indole (1l) with 2a afforded the desired products 3k (86%)and 3l (86%).

Technology Process of 5-(Trifluoromethyl)indole

There total 21 articles about 5-(Trifluoromethyl)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%

2-(2-nitro-5-(trifluoromethyl)phenyl)acetonitrile (200711-18-8) → 5-trifluoromethyl-1H-indole (100846-24-0)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 12h; under 760.051 Torr;

DOI:10.1002/adsc.201700374

Reference yield: 88.0%

cyano-(2-nitro-5-trifluoromethyl-phenyl)-acetic acid benzyl ester → 5-(trifluoromethyl)indoline (162100-55-2) + 5-trifluoromethyl-1H-indole (100846-24-0) + 2-(2-amino-ethyl)-4-trifluoromethyl-phenylamine

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In ethanol; water; at 25 ℃; for 18h; under 2585.74 Torr;

DOI:10.1081/SCC-120021501

Reference yield: 77.0%

N-[2-(3,3-dimethyl-3-silabut-1-ynyl)-4-(trifluoromethyl)phenyl]ethoxycarboxamide (1217302-64-1) → 5-trifluoromethyl-1H-indole (100846-24-0)

Guidance literature:

With sodium ethanolate; In ethanol; for 2h; Reflux;

upstream raw materials:

3-iodo-5-trifluoromethyl-1H-indole

2-(2-trimethylsilylethynyl)-4-trifluoromethylaniline

3-chloro-4-nitrobenzotrifluoride

4-trifluoromethylphenylamine

Downstream raw materials:

6-(trifluoromethyl)-2,3,4,9,-tetrahydro-1H-carbazole

Refernces

• 1、 Danoun, Grégory,Bayarmagnai, Bilguun,Grünberg, Matthias F.,Goo?en, Lukas J.. "Sandmeyer trifluoromethylation of arenediazonium tetrafluoroborates". . p. 7972 - 7975. Retrieved 2013.
• 2、 Hong, Zonghan,Chong, Wee Kiang,Ng, Andrew Yun Ru,Li, Mingjie,Ganguly, Rakesh,Sum, Tze Chien,Soo, Han Sen. "Hydrophobic Metal Halide Perovskites for Visible-Light Photoredox C?C Bond Cleavage and Dehydrogenation Catalysis". . p. 3456 - 3460. Retrieved 2019/02/13.
• 3、 Choi, Isaac,Chung, Hyunho,Park, Jang Won,Chung, Young Keun. "Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions". . p. 5508 - 5511. Retrieved 2016/11/17.