2,8-Bis(trifluoromethyl)quinoline-4-carbaldehyde

Base Information

• Chemical Name: 2,8-Bis(trifluoromethyl)quinoline-4-carbaldehyde
• CAS No.: 57120-56-6
• Molecular Formula: C₁₂H₅F₆NO
• Molecular Weight: 293.168
• DSSTox Substance ID: DTXSID901228822
• Nikkaji Number: J2.965.837D
• Mol file: 57120-56-6.mol

Synonyms:2,8-bis(trifluoromethyl)quinoline-4-carbaldehyde;2,8-bis(trifluoromethyl)-4-quinolinecarboxaldehyde;57120-56-6;SCHEMBL1147111;DTXSID901228822

Chemical Property of 2,8-Bis(trifluoromethyl)quinoline-4-carbaldehyde

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 293.02753276
• Heavy Atom Count: 20
• Complexity: 366

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)C(F)(F)F)N=C(C=C2C=O)C(F)(F)F

Technology Process of 2,8-Bis(trifluoromethyl)quinoline-4-carbaldehyde

There total 1 articles about 2,8-Bis(trifluoromethyl)quinoline-4-carbaldehyde 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:

mefloquine hydrochloride (68682-28-0) → 2,8-bis(trifluoromethyl)quinolin-4-ol (35853-41-9) + 2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde (57120-56-6) + 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid (35853-50-0) + 2-oxo-8-trifluoromethyl-1,2-dihydro-quinoline-4-carbaldehyde

Guidance literature:

With sodium hydroxide; potassium dihydrogenphosphate; oxygen; In methanol; water; for 0.583333h; pH=7.4; Further Variations:; pH-values; Reagents; Solvents; O2 conc., ionic strength, buffer conc., addition of scavengers; Kinetics; Quantum yield; Irradiation;

Reference yield: 69.0%

2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde (57120-56-6) + C18H21ClN2O2 → C30H25F6N3O3 + C30H25F6N3O3

Guidance literature:

C₁₈H₂₁ClN₂O₂; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol2010193

Reference yield:

2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde (57120-56-6) → C20H11F6NO3

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / pentan-3-one / 18 h / 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / Inert atmosphere; Reflux

With n-butyllithium; toluene-4-sulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; pentan-3-one; 1.1: Darzens condensation / 1.2: Darzens condensation / 3.1: Baeyer-Villiger oxidation;

DOI:10.1021/ol2010193

upstream raw materials:

mefloquine hydrochloride

Downstream raw materials:

(-)-syn-mefloquine hydrochloride

(+)-threo-mefloquine hydrochloride

(R)-2-((S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium chloride

(2,8-bis-trifluoromethyl-quinolin-4-yl)-piperidin-2-yl-methanol; hydrochloride