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

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

Downstream Products

• 131747-57-4 (2-(trifluoromethyl)pyridin-3-yl)methanol 
• 1018678-39-1 4-chloro-2-(trifluoromethyl)nicotinic acid 
• 116308-35-1 2-(trifluoromethyl)-3-pyridinecarboxaldehyde 
• 108337-84-4 2-(N-Benzyl-N-methylamino)ethyl Methyl 4-(2-Trifluoromethyl-3-pyridyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 104326-73-0 4-(trifluoromethyl)pyridine-3-carbonyl chloride 
• 910054-29-4 N-(3',4'-dichlorobiphenyl-2-yl)-2-trifluoromethyl-nicotinamide 
• 923288-07-7 3,4-bis(benzyloxy)-5-nitro-N'-(2-(trifluoromethyl)nicotinoyloxy)benzimidamide 
• 1227070-39-4 N-(1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl)-N-methyl-2-(trifluoromethyl)nicotinamide 
• 1244760-80-2 C₂₄H₂₅F₃N₆O 
• 1261276-06-5 C₃₀H₂₂F₄N₄O₃S 
• 119899-27-3 2-(trifluoromethyl)pyridine-3-carbonyl chloride 
• 870101-37-4 ethyl 4-amino-2-(trifluoromethyl)nicotinate 
• 1060814-58-5 3-(chloromethyl)-2-(trifluoromethyl)pyridine 
• 2107987-89-1 O-ethyl S-((2-(trifluoromethyl)pyridin-3-yl)methyl)carbonodithioate 

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.

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).