131747-41-6

Basic information

• Product Name: 2-(Trifluoromethyl)isonicotinic acid
• Synonyms: 2-(Trifluoromethyl)pyridine-4-carboxylic acid, 4-Carboxy-2-(trifluoromethyl)pyridine;2-(TRIFLUOROMETHYL)ISONICOTINIC ACID;2-(Trifluoromethyl)pyridine-4-carBoxylicacid;2-(Trifluoromethyl)isonicotinicacid97%;2-trifluoromethyl-4-pyridinecarboxylic acid;2-(Trifluoromethyl)isonicotinic acid 97%;2-(trifluoroMethyl)pyridin-4-carboxylic acid;4-Pyridinecarboxylicacid, 2-(trifluoroMethyl)-
• CAS NO: 131747-41-6
• Molecular Formula: C₇H₄F₃NO₂
• Molecular Weight: 191.11
• Product Categories: Pyridine series;Carboxylic Acids;Pyridines;Carboxylic Acids
• Mol File: 131747-41-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 217-223℃
• Boiling Point: 338.881 °C at 760 mmHg
• Flash Point: 158.75 °C
• Appearance: Off-white/Solid
• Density: 1.485 g/cm³
• Vapor Pressure: 3.71E-05mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 2.94±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2-(Trifluoromethyl)isonicotinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethyl)isonicotinic acid(131747-41-6)
• EPA Substance Registry System: 2-(Trifluoromethyl)isonicotinic acid(131747-41-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 131747-41-6(Hazardous Substances Data)

Usage

Uses

2-(Trifluoromethyl)isonicotinic Acid is useful reactant for the preparation of RAF709 as selective RAF inhibitor targeting RAS mutant cancer.

InChI:InChI=1/C7H4F3NO2/c8-7(9,10)5-3-4(6(12)13)1-2-11-5/h1-3H,(H,12,13)

Upstream product

• 124-38-9 carbon dioxide 
• 368-48-9 2-(trifluoromethyl)pyridine 
• 1621525-59-4 4-(furan-2-yl)-2-(trifluoromethyl)pyridine 
• 208265-51-4 1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-one 
• 66572-56-3 2-bromoisonicotinic acid 
• 170886-13-2 4-hydroxy-2-trifluoromethylpyridine 
• 131748-14-6 4-chloro-2-trifluoromethylpyridine 
• 916210-02-1 2-(trifluoromethyl)pyridine-4-carbonitrile 
• 201230-82-2 carbon monoxide 
• 590371-73-6 2-(trifluoromethyl)pyridine-4-iodide 
• 590371-71-4 3-iodo-2-(trifluoromethyl)pyridine 
• 75-24-1 trimethylaluminum 

Downstream Products

• 588702-68-5 2-trifluoromethyl-isonicotinic acid methyl ester 
• 1214351-44-6 2-trifluoromethyl-isonicotinic acid ethyl ester 

Relevant articles and documents

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

PROCESS FOR THE PREPARATION OF 2-TRIFLUOROMETHYL ISONICOTINIC ACID AND ESTERS

The invention relates to a novel process for the preparation of 2- trifluoromethyl isonicotinic acid and esters of the formula I which involves a palladium catalysed carbonylation or cyanation step wherein R1 is hydrogen or Q1-6-alkyl. The 2-trifluoromethyl isonicotinic acid and esters of the formula I are versatile intermediates for the preparation of active pharmaceutical and agrochemical agents such as for instance TAAR 1 agonists of the formula III.

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).