175880-30-5

Basic information

• Product Name: Pyridinium, 1-(difluoromethyl)-4-(dimethylamino)-, bromide (1:1)
• Synonyms: Pyridinium, 1-(difluoromethyl)-4-(dimethylamino)-, bromide (1:1)
• CAS NO: 175880-30-5
• Molecular Formula: C8H11F2N2.Br
• Molecular Weight: 253.089
• Mol File: 175880-30-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyridinium, 1-(difluoromethyl)-4-(dimethylamino)-, bromide (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridinium, 1-(difluoromethyl)-4-(dimethylamino)-, bromide (1:1)(175880-30-5)
• EPA Substance Registry System: Pyridinium, 1-(difluoromethyl)-4-(dimethylamino)-, bromide (1:1)(175880-30-5)

Safety Data

• Hazardous Substances Data: 175880-30-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11F2N2.BrH/c1-11(2)7-3-5-12(6-4-7)8(9)10;/h3-6,8H,1-2H3;1H/q+1;/p-1

Upstream product

• 1122-58-3 dmap 
• 75-52-5 nitromethane 
• 667-27-6 Ethyl bromodifluoroacetate 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 

Relevant articles and documents

A simple method for the synthesis of: N -difluoromethylated pyridines and 4-pyridones/quinolones by using BrCF2COOEt as the difluoromethylation reagent

We describe a novel transition metal-free method for the synthesis of N-difluoromethylated pyridines and 4-pyridones/quinolones by using readily available ethyl bromodifluoroacetate as a fluorine source. The formation of N-difluoromethylated pyridines involves a two-step process in which N-alkylation by ethyl bromodifluoroacetate is followed by in situ hydrolysis of the ester and decarboxylation. Besides optimizing the N-difluoromethylation conditions and assessing the influence of steric and electronic effects on the outcome of the reaction, we have synthesized the N-difluoromethylated analogues of two fluorophores and demonstrated that their spectroscopic properties can be improved through replacement of N-CH3 group by N-CF2H. This journal is

Direct Synthesis of N-Difluoromethyl-2-pyridones from Pyridines

A novel method for the synthesis of N-difluoromethyl-2-pyridones was described. This protocol enables the synthesis of N-difluoromethyl-2-pyridones from readily available pyridines using mild reaction conditions that are compatible with a wide range of functional groups. The preliminary mechanistic study revealed that N-difluoromethylpyridinium salts were the key intermediates to complete this conversion.

Chemoselective N-Difluoromethylation of Functionalized Tertiary Amines

A practical, convenient, and general method for the difluoromethylation of tertiary amines, using diethyl bromodifluoromethylphosphonate and fluoride, is described. This commercially available phosphonate smoothly reacts with a fluoride ion to liberate a difluorocarbene intermediate that in the presence of a proton source and a tertiary amine generates the corresponding α-difluoromethylammonium compound in good to excellent yields. Despite the involvement of a difluorocarbene intermediate, this difluoromethylation occurs almost exclusively on the nitrogen atom with diverse molecular structures, including drugs, surfactants, chiral phase transfer catalysts, polymers, ionic liquids, and other fine chemicals. A preliminary assessment of the effects that an α-difluoromethyl groupT has on hydrogen bonding and logP of quaternary ammonium salts is also described.