131747-43-8

Basic information

• Product Name: 3-Pyridinecarboxylicacid, 2-(trifluoromethyl)-
• Synonyms: 2-(Trifluoromethyl)nicotinicacid;2-(Trifluoromethyl)pyridine-3-carboxylic acid
• CAS NO: 131747-43-8
• Molecular Formula: C₇H₄F₃NO₂
• Molecular Weight: 191.1074
• EINECS: 223-090-5
• Product Categories: Building Blocks;Pyridine;Aromatics Compounds;Aromatics;Heterocycles;Carboxylic Acids;Carboxylic Acids;Pyridines;Heterocycle
• Mol File: 131747-43-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 184-188℃
• Boiling Point: 259.9 °C at 760 mmHg
• Flash Point: 111 °C
• Appearance: /
• Density: 1.484 g/cm³
• Vapor Pressure: 0.00642mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol (Slightly)
• PKA: 2.50±0.36(Predicted)
• CAS DataBase Reference: 3-Pyridinecarboxylicacid, 2-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylicacid, 2-(trifluoromethyl)-(131747-43-8)
• EPA Substance Registry System: 3-Pyridinecarboxylicacid, 2-(trifluoromethyl)-(131747-43-8)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: 26-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 131747-43-8(Hazardous Substances Data)

Usage

Description

3-Pyridinecarboxylic acid, 2-(trifluoromethyl)-, also known as 2-trifluoromethylnicotinic acid, is an organic compound with the molecular formula C7H4F3NO2. It is a white to light brown powder or crystal at room temperature. 3-Pyridinecarboxylicacid, 2-(trifluoromethyl)is characterized by its trifluoromethyl group attached to the pyridine ring, which imparts unique chemical and biological properties to the molecule.

Uses

Used in Agrochemical Industry:
3-Pyridinecarboxylic acid, 2-(trifluoromethyl)-, is used as an intermediate for agrochemical fungicides. Its application in this industry is due to its ability to serve as a key building block in the synthesis of various fungicidal compounds. These compounds are effective in controlling fungal infections in crops, thereby improving agricultural productivity and crop quality.
As an intermediate, 3-Pyridinecarboxylic acid, 2-(trifluoromethyl)-, can be further modified or functionalized to create a range of fungicides with different modes of action and target specific fungal pathogens. This versatility makes it a valuable component in the development of new and improved agrochemical products to address the ever-evolving challenges in crop protection.

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

Upstream product

• 124-38-9 carbon dioxide 
• 368-48-9 2-(trifluoromethyl)pyridine 
• 208517-35-5 ethyl 2-(trifluoromethyl)pyridine-3-carboxylate 
• 2942-59-8 2-chloronicotinic acid 
• 77152-08-0 trifluoromethylcopper(I) 
• 3430-17-9 2-bromo-3-picoline 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 408502-43-2 3-bromo-2-iodo-pyridine 
• 77332-76-4 2-chloro-3-(trimethylsilyl)pyridine 
• 13534-89-9 2,3-dibromopyridine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 590371-58-7 3-bromo-2-(trifluoromethyl)pyridine 
• 1620-78-6 3-methyl-2-(trifluoromethyl)pyridine 

Downstream Products

• 1060814-58-5 3-(chloromethyl)-2-(trifluoromethyl)pyridine 
• 2107987-89-1 O-ethyl S-((2-(trifluoromethyl)pyridin-3-yl)methyl)carbonodithioate 
• 136483-17-5 methyl 2-trifluoromethyl-3-pyridinecarboxylate 
• 923288-08-8 3-[3-[3,4-bis(benzyloxy)-5-nitrophenyl]-[1,2,4]-oxadiazol-5-yl]-2-(trifluoromethyl)pyridine 
• 870101-37-4 ethyl 4-amino-2-(trifluoromethyl)nicotinate 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF HALOALKYL DERIVATIVES OF NICOTINIC ACID

The present invention provides a process for the preparation of a compound of Formula (I). wherein R1 is C1-C12 haloalkyl.

A practical synthesis of 4-amino-2-(trifluoromethyl)nicotinic acid

A practical synthesis of 4-amino-2-(trifluoromethyl)-nicotinic acid is described. 2-(Trifluoromethyl)pyridine was lithiated using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in the presence of 1,3-dimethyl-2- imidazolidinone (DMI) and followed by CO2 quench to give the C-3 carboxylation product. Subsequent directed C-4 lithiation of carboxylation product afforded 4-iodo-2-(trifluoromethyl)nicotinic acid, which was coupled with tert-butyl carbamate under Pd-catalyzed conditions and followed by Boc deprotection to yield the title product in four steps and 50% overall yield. Georg Thieme Verlag Stuttgart New York.

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).