135183-02-7

Basic information

• Product Name: Pyridine, 2-(fluoromethyl)-4,6-dimethyl- (9CI)
• Synonyms: Pyridine, 2-(fluoromethyl)-4,6-dimethyl- (9CI)
• CAS NO: 135183-02-7
• Molecular Formula: C8H10FN
• Molecular Weight: 139.1701032
• Product Categories: PYRIDINE
• Mol File: 135183-02-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyridine, 2-(fluoromethyl)-4,6-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-(fluoromethyl)-4,6-dimethyl- (9CI)(135183-02-7)
• EPA Substance Registry System: Pyridine, 2-(fluoromethyl)-4,6-dimethyl- (9CI)(135183-02-7)

Safety Data

• Hazardous Substances Data: 135183-02-7(Hazardous Substances Data)

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 107264-00-6 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate 

Relevant articles and documents

A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis

The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.

N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: Electrophilic fluorination of imines and some methyl-substituted pyridines

Direct fluorination of imines with N-fluoro-bis[(trifluoromethyl)sulfonyl]imide 1 afforded mono and/or difluoroketones without the need of a strong base to first generate the imine anions. Structurally related 2- and 4-methyl-substituted pyridines gave the respective fluoromethyl pyridines with 1. Our results suggest that an enamine intermediate plays a key role in these reactions.

Synthesis and Properties of N-Fluoropyridinium Salts

Various stable N-fluoropyridinium salts with a non- or weakly nucleophilic counter anion such as TfO-, FSO3-, BF4-, ClO4-, CH3SO3- etc., or with an electron-donating or -withdrawing substituent(s) on the pyridine ring were synthesized and their properties investigated.N-Fluoropyridinium-2-sulfonates, N-fluoroquinolinium triflate, and highly hindered N-fluoro-2,6-di-t-butylpyridinium salts were also synthesized.They were synthesized by counter anion displacement reactions of unstable pyridine-F2 conpounds, fluorination of salts of pyridines with protonic acids or silyl esters with F2, and/or fluorination of Lewis acid complexes of pyridines.The scope of each method was examined in detail.Each of the N-fluoropyridinium salts was assigned as the first stable 1:1 salt structure of the pyridine nucleus and halogen atom on the basis of the spectral and elemental analysis.The stability depended on the nucleophilicity or basicity of the counter anions and electronic nature or position of the ring substituents.These results and NMR analyses clearly showed the unstable pyridine-F2 compounds to have N-fluoropyridinium fluoride salt structure.Some N-fluoropyridinium triflates were hydrolyzed and the products were examined, suggesting a unique hydrolysis mechanism.