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

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

Uses

Used in Pharmaceutical Industry:
Methyl 2-(difluoroMethyl) isonicotinate is used as a building block in the synthesis of pharmaceuticals for its unique chemical properties and high level of fluorine content. It contributes to the development of fluorine-containing compounds, which are known for their enhanced biological activity and improved pharmacokinetic properties.
Used in Agrochemical Industry:
In the agrochemical industry, Methyl 2-(difluoroMethyl) isonicotinate is used as a building block in the synthesis of agrochemicals. Its fluorinated nature and unique chemical properties make it valuable in the development of more effective and environmentally friendly pesticides and other agrochemical products.
Used in Organic Synthesis:
Methyl 2-(difluoroMethyl) isonicotinate is used as a versatile ingredient in organic synthesis due to its unique chemical properties. It can be used to synthesize a wide range of compounds, including pharmaceuticals, agrochemicals, and other commercial products.
Used in Medicinal Chemistry:
In medicinal chemistry, Methyl 2-(difluoroMethyl) isonicotinate is used for its potential applications in the development of new drugs and therapeutic agents. Its fluorinated nature and unique chemical properties can enhance the biological activity and pharmacokinetic properties of the synthesized compounds, leading to more effective treatments for various diseases and conditions.

Upstream product

• 381-73-7 Difluoroacetic acid 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 
• 58481-11-1 methyl 2-chloroisonicotinate 
• 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.

Direct Csp2?H difluoromethylation of heterocycle by K2S2O8

We reveal here a novel and efficient transition-metal-free C(sp2)–H oxidative difluoromethylation of heterocycle. It uses stable and nontoxic NaSO2CF2H as difluoromethyl source and potassium persulfate as oxidant without the need for metal catalyst. Significantly, the reaction affords difluoromethyl heterocycles in moderate to good yields with a broad substrate tolerance.

Difluoroacetic Acid as a New Reagent for Direct C?H Difluoromethylation of Heteroaromatic Compounds

A technically simple procedure for direct C?H difluoromethylation of heteroaromatic compounds using off-the-shelf difluoroacetic acid as the difluoromethylating reagent has been developed. Mono-difluoromethylation versus bis-difluoromethylation is controlled as the result of the reaction temperature. The reactions described here enable access to the late-stage C?H mono- and bis-difluoromethylation for preparation of tool compounds for chemical biology and provide access to this hitherto untapped substituent for drug discovery.

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.

NOVEL COMPOUNDS

Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

ISOXAZOL-3(2H)-ONE ANALOGS AS THERAPEUTIC AGENTS

or a pharmaceutically suitable salt thereof, wherein, R1 and R2 independently are hydrogen, deuterium, aryl, hetero aryl, C1-C8 alkyl, optionally being substituted with one or more substituents independently being R3,R3 is an aryl, hetero aryl, fluorine(s), a C1-C6 alkyl containing one or more fluorine, a C1-C6 alkyl containing one or more deuterium, a C1-C6 alkyl containing hydroxy, the aryl and heteroaryl optionally being substituted with one or more halogen, a fluorinated alkoxy, a fluorinated alkyl, a sulfonyl, one or more deuterium, a C1-6 alkyl, a C1-6 alkoxy, a nitrile,or R3 is a C1-6 alkyl optionally substituted with one or more of the following groups: COOR4, OCOR4, CONR5R6, NR5COR6, OR4;wherein, R4 is a C1-10 alkyl optionally substituted with one or more fluorine, deuterium, alkoxy, arylcarboxylate, alkyl carboxylate;R5 and R6 are independently selected from hydrogen, alkyl or they may together form a 4-8 membered carbon ring;or R1 and R2 form a 3-10 membered carbon ring optionally comprising O or N and optionally substituted with a C1-10 alkyl or aryl, hetero aryl optionally substituted with R3.