1251844-44-6

Basic information

• Product Name: Methyl 2-(difluoroMethyl) isonicotinate
• Synonyms: Methyl 2-(difluoroMethyl) isonicotinate;Methyl 2-(difluoromethyl)pyridine-4-carboxylate, 2-(Difluoromethyl)-4-(methoxycarbonyl)pyridine;Methyl 2-(difluoroMethyl)pyridine-4-carboxylate;ethyl 2-(difluoroMethyl)isonicotinate
• CAS NO: 1251844-44-6
• Molecular Formula: C8H7F2NO2
• Molecular Weight: 187.143
• Mol File: 1251844-44-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 2-(difluoroMethyl) isonicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(difluoroMethyl) isonicotinate(1251844-44-6)
• EPA Substance Registry System: Methyl 2-(difluoroMethyl) isonicotinate(1251844-44-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 1251844-44-6(Hazardous Substances Data)

Usage

General Description

Methyl 2-(difluoroMethyl) isonicotinate is a chemical compound with the molecular formula C8H7F2NO2. It is a yellow liquid with a faint odor, and is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is classified as a fluorinated aromatic ester, and its high level of fluorine content makes it valuable in the development of fluorine-containing compounds for various applications. Methyl 2-(difluoroMethyl) isonicotinate is also known for its use in organic synthesis and medicinal chemistry, and its unique chemical properties make it a versatile and important ingredient in the production of various commercial products.

Upstream product

• 58481-11-1 methyl 2-chloroisonicotinate 
• 381-73-7 Difluoroacetic acid 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 
• 275818-95-6 sodium difluoromethanesulfinate 
• 131747-63-2 4-bromo-2-pyridinecarboxaldehyde 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1211580-54-9 4-bromo-2-(difluoromethyl)pyridine 
• 125104-34-9 methyl 2-formylpyridine-4-carboxylate 

Downstream Products

• 1256818-14-0 2-(difluoromethyl)isonicotinic acid 

Relevant articles and documents

2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: The case of quorum sensing inhibitors

Herein, we demonstrate that 2-difluoromethylpyridine is a bioisosteric replacement of pyridine-N-oxide. Using the quorum sensing inhibitor 4NPO as a model compound, a library of 2-difluoromethylpyridine derivatives was designed, synthesized, and evaluated toward quorum sensing activity, biofilm formation, anti-violacein activity, and protease activity. As a result, compounds1(IC50of 35 ± 1.12 μM),5(IC50of 19 ± 1.01 μM), and6(IC50of 27 ± 0.67 μM) showed a similar or better activity in comparison to (IC50of 33 ± 1.12 μM) in a quorum sensing system ofPseudomonas aeruginosa. In addition, compounds1,5,6, and showed good antibiofilm biomass ofPseudomonas aeruginosaand reduced violacein production inChromobacterium violaceum. In terms of protease activity, compounds1,5, and6showed significant activity compared 4NPO. Overall, the replacement of pyridine-N-oxide by 2-difluoromethylpyridine enhances the activity of the model compound, which could open a new path for bioisosteric replacement in drug discovery and development.

Palladium-catalyzed difluoromethylation of heteroaryl chlorides, bromides and iodides

A palladium-catalyzed difluoromethylation of a series of heteroaryl chlorides, bromides and iodides under mild conditions is described. A wide range of heteroaryl halides such as pyridyl, pyrimidyl, pyrazyl, funanyl, thienyl, pyazolyl, imidazolyl, thiazolyl, and oxazolyl halides were efficiently difluoromethylated, thus providing medicinal chemists an alternative choice for the preparation of drug candidates with the difluoromethylated heteroarene unit.

Sodium difluoromethanesulfinate—A difluoromethylating agent toward protonated heterocyclic bases

Free radical difluoromethylation of protonated heteroaromatic bases was accomplished using sodium difluoromethanesulfinate in combination with tert-butyl hydroperoxide in a two-phase system (methylene chloride–water) at room temperature. The difluoromethylation products of methyl pyridine-4-carboxylate, pyridine-4-carbonitrile, and 2-amino-1,3,4-thiadiazole were isolated on a preparative scale.