35853-55-5

Basic information

• Product Name: bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone
• Synonyms: bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone;2-Pyridyl-2,8-bis(trifluoromethyl)-4-quinolyl ketone ;[2,8-Bis(trifluoromethyl)-4-quinolyl]2-pyridyl ketone;2-Pyridinyl[2,8-bis(trifluoromethyl)-4-quinolinyl]methanone;4-[3-({2-[2,8-bis(trifluoroMethyl)quinolin-4-yl]pyridin-3-yl}carbonyl)pyridin-2-yl]-2,8-bis(trifluoroMethyl)quinoline;Methanone, [2,8-bis(trifluoroMethyl)-4-quinolinyl]-2-pyridinyl-;[2,8-Bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanone;Mefloquine EP impurity A
• CAS NO: 35853-55-5
• Molecular Formula: C₁₇H₈F₆N₂O
• Molecular Weight: 712.4871784
• EINECS: 252-763-6
• Mol File: 35853-55-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 427.828 °C at 760 mmHg
• Flash Point: 212.543 °C
• Appearance: /
• Density: 1.451
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone(CAS DataBase Reference)
• NIST Chemistry Reference: bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone(35853-55-5)
• EPA Substance Registry System: bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone(35853-55-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 35853-55-5(Hazardous Substances Data)

Usage

Description

Bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone is a complex organic compound characterized by its unique molecular structure, featuring two quinolinyl and pyridyl groups connected through a central ketone bridge. bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone is known for its potential applications in various fields due to its distinct chemical properties.

Uses

Used in Pharmaceutical Industry:
Bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone is used as an intermediate in the synthesis of Mefloquine Hydrochloride (M207052), a labeled quinoline methanol antimalarial agent. Its role in the synthesis process is crucial for the development of effective treatments against malaria, a disease that affects millions of people worldwide.
bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone's specific structural features allow it to contribute to the overall effectiveness of Mefloquine Hydrochloride, which is known for its ability to combat Plasmodium parasites responsible for malaria. By being a part of the synthesis process, bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone plays a significant role in the pharmaceutical industry's efforts to combat this global health issue.

InChI:InChI=1/C17H8F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h1-8H

Upstream product

• 941279-81-8 2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol 
• 17624-36-1 2-pyridyllithium 
• 35853-50-0 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid 
• 35853-45-3 (2,8-bis-trifluoromethyl)-4-bromoquinoline 
• 83012-13-9 2,8-bis-(trifluoromethyl)-4-chloro-quinoline 
• 2739-97-1 pyridine-2-acetonitrile 
• 123590-69-2 4-<(tert-butyldimethylsilyl)(2-pyridyl)methoxy>-2,8-bis(trifluoromethyl)quinoline 
• 123559-29-5 4-(2-pyridylmethoxy)-2,8-bis(trifluoromethyl)quinoline 
• 6959-47-3 2-chloromethylpyridine hydrochloride 
• 35853-41-9 2,8-bis(trifluoromethyl)quinolin-4-ol 
• 68496-04-8 [2,8-bis(trifluoromethyl)quinolin-4-yl]pyridin-2-ylmethanol 
• 138058-60-3 α-Hydroxy-α-(2-pyridyl)-2,8-bis(trifluoromethyl)-4-quinolylacetonitrile 
• 83012-12-8 α-(2-Pyridyl)-2,8-bis(trifluoromethyl)-4-quinolylacetonitrile 

Downstream Products

• 49752-90-1 (+/-)-mefloquine 
• 51744-85-5 (+)-threo-mefloquine hydrochloride 
• 68682-28-0 (R)-2-((S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium chloride 
• 51773-92-3 mefloquine hydrochloride 

Relevant articles and documents

An expedient and high yielding synthesis of mefloquine, via fluoride ion-catalyzed wittig rearrangement I

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Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.

ONE POT SYNTHESIS OF [2, 8-BIS (TRIFLUOROMETHYL)-4- QUINOLINYL]2-PYRIDINYLMETHANONE, A MEFLOQUINE INTERMEDIATE

The present invention provides a simple single step process for the preparation of [2,8-bis (trifluoromethyl)-4-quinolinyl]-2 -pyridinylmethanone, comprising the step of condensing a halo-quinoline with an alpha-picolyl derivatives in the presence of a solvent, a base and a phase transfer catalyst at ?10° C. to +90° C.