5-(Trifluoromethyl)-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 5-(Trifluoromethyl)-1,2,3,4-tetrahydroquinoline
• CAS No.: 939758-74-4
• Molecular Formula: C₁₀H₁₀F₃N
• Molecular Weight: 201.191
• European Community (EC) Number: 843-011-3
• DSSTox Substance ID: DTXSID30585673
• Wikidata: Q82477672
• Mol file: 939758-74-4.mol

Synonyms:5-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline;939758-74-4;5-Trifluoromethyl-1,2,3,4-tetrahydro-quinoline hydrochloride;SCHEMBL19776019;DTXSID30585673;ANAKGDXHTHSQBX-UHFFFAOYSA-N;MFCD08544267;AKOS037621892;EN300-208789;1,2,3,4-tetrahydro-5-(trifluoromethyl)-Quinoline

Chemical Property of 5-(Trifluoromethyl)-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Boiling Point: 234.4±40.0 °C(Predicted)
• PKA: 4.11±0.20(Predicted)
• PSA: 12.03000
• Density: 1.213±0.06 g/cm3(Predicted)
• LogP: 3.20150
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 201.07653381
• Heavy Atom Count: 14
• Complexity: 202

Purity/Quality:

98%min ^*data from raw suppliers

5-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CC=C2NC1)C(F)(F)F

Technology Process of 5-(Trifluoromethyl)-1,2,3,4-tetrahydroquinoline

There total 3 articles about 5-(Trifluoromethyl)-1,2,3,4-tetrahydroquinoline 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%

tert-butyl (tosyloxy)(3-(2-(trifluoromethyl)phenyl)propyl)carbamate → 5-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline (939758-74-4)

Guidance literature:

With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; trifluoroacetic acid; In 2,2,2-trifluoroethanol; at 0 - 20 ℃; for 23h; regioselective reaction;

DOI:10.1126/science.aaf8713

Reference yield: 68.0%

5-(trifluoromethyl)quinolone (342-30-3) → 5-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline (939758-74-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 112511 Torr;

DOI:10.1021/acs.joc.9b03011

Reference yield:

quinoline-5-carboxylic acid (7250-53-5) → 5-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline (939758-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen fluoride; sulfur tetrafluoride / 24 h / 85 °C / Autoclave; Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 20 °C / 112511 Torr

With palladium 10% on activated carbon; sulfur tetrafluoride; hydrogen fluoride; hydrogen; In methanol;

DOI:10.1021/acs.joc.9b03011

upstream raw materials:

5-(trifluoromethyl)quinolone

quinoline-5-carboxylic acid

Refernces

• 1、 Alekseenko, Anatoliy N.,Bugera, Maksym Ya.,Gerus, Igor I.,Kiriakov, Oleksandr,Klipkov, Anton A.,Mykhailiuk, Pavel K.,Pustovit, Yurii,Razhyk, Bohdan,Semenov, Sergey,Starova, Viktoriia S.,Tananaiko, Oksana Yu.,Tarasenko, Karen,Tolmachev, Andrei A.,Trofymchuk, Serhii,Zaporozhets, Olga A.. "Deoxofluorination of (Hetero)aromatic Acids". . p. 3110 - 3124. Retrieved 2020/03/23.
• 2、 Paudyal, Mahesh P.,Adebesin, Adeniyi Michael,Burt, Scott R.,Ess, Daniel H.,Ma, Zhiwei,Kürti, László,Falck, John R.. "Dirhodium-catalyzed C-H arene amination using hydroxylamines". . p. 1144 - 1147. Retrieved 2016/11/09.