587886-26-8

Basic information

• Product Name: 2-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID
• Synonyms: 2-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID;3-Quinolinecarboxylic acid, 2-(trifluoroMethyl)-
• CAS NO: 587886-26-8
• Molecular Formula: C11H6F3NO2
• Molecular Weight: 241.17
• EINECS: 604-604-1
• Product Categories: Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 587886-26-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 207-209 °C(Solv: methanol (67-56-1))
• Boiling Point: 321.2 °C at 760 mmHg
• Flash Point: 148.1 °C
• Appearance: /
• Density: 1.481 g/cm³
• Vapor Pressure: 0.000125mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: 2-8°C
• PKA: 2.42±0.30(Predicted)
• CAS DataBase Reference: 2-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID(587886-26-8)
• EPA Substance Registry System: 2-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID(587886-26-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 587886-26-8(Hazardous Substances Data)

Usage

General Description

2-(Trifluoromethyl)quinoline-3-carboxylic acid is a chemical compound that consists of a quinoline ring with a carboxylic acid group and a trifluoromethyl substituent. It is used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. The trifluoromethyl group imparts unique properties to the molecule, making it useful in drug discovery and development. 2-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID has potential application in anti-inflammatory, antiviral, and anticancer drug development due to its structural features and reactivity. Its versatile chemical nature makes it valuable for medicinal and synthetic chemistry research.

InChI:InChI=1/C11H6F3NO2/c12-11(13,14)9-7(10(16)17)5-6-3-1-2-4-8(6)15-9/h1-5H,(H,16,17)

Upstream product

• 347-42-2 2-trifluoromethyl-quinoline 
• 124-38-9 carbon dioxide 
• 587886-31-5 methyl 2-(trifluoromethyl)quinoline-3-carboxylate 
• 587886-11-1 4-bromo-2-trifluoromethyl-3-quinolinecarboxylic acid 
• 83842-55-1 2‐(trifluoromethyl)quinolin‐4(1H)‐one 
• 62-53-3 aniline 
• 18706-25-7 4-bromo-2-(trifluoromethyl)quinoline 
• 587886-19-9 4-bromo-2-trifluoromethyl-3-quinolinecarboxylic acid methyl ester 

Relevant articles and documents

Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones

The acid-catalyzed cyclization-condensation between anilines and ethyl 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones (1), which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. These undergo halogen/metal exchange, generating 2-trifluoromethyl-4-quinolyllithiums, when treated with butyllithium, and hydrogen/metal exchange, generating 4-bromo-2-trifluoromethyl-3-quinolyllithiums, when treated with lithium diisopropylamide. Trapping of the latter intermediates provides 3-functionalized products that may be further elaborated by electrophilic substitution of the bromine atom. A few unexpected findings resulted from these investigations, the most noteworthy being an unprecedented buttressing effect and a counterintuitive halogen reactivity. ( 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).