588702-64-1

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
3-(TRIFLUOROMETHYL)QUINOLINE-2-CARBOXYLIC ACID is used as a building block for the synthesis of various biologically active molecules, leveraging its trifluoromethyl substituent to enhance the properties and activities of the resulting compounds.
Used in Drug Design and Discovery:
3-(TRIFLUOROMETHYL)QUINOLINE-2-CARBOXYLIC ACID is utilized as a key component in drug design and discovery, due to its ability to modulate the properties of compounds, potentially leading to the development of new drugs for a range of diseases.
Used in the Development of New Drugs for Cancer:
3-(TRIFLUOROMETHYL)QUINOLINE-2-CARBOXYLIC ACID is used as a potential component in the development of new drugs for cancer treatment, given its role in modulating the biological activities of synthesized compounds.
Used in the Development of New Drugs for Infectious Diseases:
3-(TRIFLUOROMETHYL)QUINOLINE-2-CARBOXYLIC ACID is used as a potential building block in the development of new drugs for infectious diseases, due to its ability to influence the properties of synthesized molecules.
Used in the Development of New Drugs for Neurological Disorders:
3-(TRIFLUOROMETHYL)QUINOLINE-2-CARBOXYLIC ACID is used as a component in the development of new drugs for neurological disorders, potentially contributing to the creation of effective treatments through its influence on the properties of synthesized compounds.

Upstream product

• 124-38-9 carbon dioxide 
• 590371-95-2 2-bromo-3-(trifluoromethyl)quinoline 
• 128676-85-7 2-chloro-3-iodo-quinoline 
• 25199-86-4 2-chloro-3-(trifluoromethyl)quinoline 
• 25199-76-2 3-(trifluoromethyl)quinoline 

Relevant academic research and scientific papers

Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids

As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

The direct metalation and subsequent functionalization of trifluoromethyl-substituted pyridines and quinolines

Depending on the choice of the reagent, 2-(trifluoromethyl)-pyridine can be selectively metalated and subsequently carboxylated of otherwise functionalized either at the 3- or at the 6-position. "Optional site selectivity" can also be achieved with 4-(trifluoromethyl)pyridine, which may be deprotonated either at the 2- or at the 3-position. In contrast, 3-(trifluoromethyl)pyridine undergoes nucleophilic addition and ensuing decomposition whatever the base. Depending on the reaction conditions, 2-(trifluoromethyl)quinoline displays reactivity toward lithium reagents at its 3-, 4-, or 8-positions, 3-(trifluoromethyl)quinolines at the 2- or 4-positions, and 4-(trifluoromethyl)quinoline at the 2- or 3-positions. It was therefore possible to prepare four trifluoromethyl-substituted pyridinecarboxylic acids (1, 4, 9, and 10) and six trifluoromethyl-substituted quinolinecarboxylic acids (11, 13, 14, 15, 17, and 18) regioisomerically uncontaminated and in a most straightforward way. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).