111887-71-9

Basic information

• Product Name: Pyridine, 2-fluoro-3,5-dimethyl- (9CI)
• Synonyms: Pyridine, 2-fluoro-3,5-dimethyl- (9CI);2-Fluoro-3,5-dimethylpyridine;3,5-Dimethyl-2-fluoropyridine
• CAS NO: 111887-71-9
• Molecular Formula: C7H8FN
• Molecular Weight: 125.1435232
• Product Categories: PYRIDINE
• Mol File: 111887-71-9.mol

Chemical Properties

• Boiling Point: 184.2°C at 760 mmHg
• Flash Point: 65.2°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 1.02mmHg at 25°C
• Refractive Index: 1.481
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.15±0.20(Predicted)
• CAS DataBase Reference: Pyridine, 2-fluoro-3,5-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-fluoro-3,5-dimethyl- (9CI)(111887-71-9)
• EPA Substance Registry System: Pyridine, 2-fluoro-3,5-dimethyl- (9CI)(111887-71-9)

Safety Data

• Hazardous Substances Data: 111887-71-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Pyridine, 2-fluoro-3,5-dimethyl(9CI) is used as a building block for the synthesis of more complex organic molecules due to its unique structure and properties.
Used in Pharmaceutical Applications:
Pyridine, 2-fluoro-3,5-dimethyl(9CI) is used as an intermediate in the development of new pharmaceutical compounds, taking advantage of its increased reactivity and altered chemical and physical properties.
Used in Material Development:
Pyridine, 2-fluoro-3,5-dimethyl(9CI) is used in the development of new materials, leveraging its fluorinated nature and potential for unique applications.
Used in Biological Studies:
Pyridine, 2-fluoro-3,5-dimethyl(9CI) is used in biological research to explore its potential applications and effects in various biological systems.

InChI:InChI=1/C7H8FN/c1-5-3-6(2)7(8)9-4-5/h3-4H,1-2H3

Upstream product

• 591-22-0 3,5-Lutidine 
• 116241-63-5 C₇H₉FN⁽¹⁺⁾*BF₄^(1-) 

Relevant articles and documents

C-H FLUORINATION OF HETEROCYCLES WITH SILVER (II) FLUORIDE

The present invention provides compositions and methods for the selective C-H fluorination of nitrogen-containing heteroarenes with AgF2, which has previously been considered too reactive for practical, selective C-H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of F2 gas. The present invention provides a mild and general method for the C-H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF2. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.

Selective C-H fluorination of pyridines and diazines inspired by a classic amination reaction

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochemicals, and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. We present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using commercially available silver(II) fluoride. The reactions occur at ambient temperature within 1 hour with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.

Preparation of 2-Fluoropyridines via Base-Induced Decomposition of N-Fluoropyridinium Salts

N-Fluoropyridinium salts with either BF4-, SbF6-, or PF6- as a counteranion were treated with excess base such as triethylamine at room temperature to give 2-fluoropyridine in good yield.This method was succesfully applied to the preparation of 2-fluoropyridine derivatives possessing electron-donating or -withdrawing substituents using substituted N-fluoropyridinium tetrafluoroborates.Pyridine-F2 compounds produced through reactions of pyridines with molecular fluorine were also treated with base to give 2-fluoropyridines but in low yields.These reactions are considered to occur through a carbene mechanism as follows: a novel N-F-containing cyclic carbene (3), generated from the N-fluoropyridinium salts by 2-proton abstraction, reacts with fluorine atoms from counteranions such as BF4-, SbF6-, or PF6-, followed by elimination of F- from the N-F moiety, to yield 2-fluoropyridines.Previously reported findings in reactions of pyridines with molecular fluorine are explained on the basis of this mechanism.

DIRECT FLUORINATION OF SUBSTITUTED PYRIDINES

The direct fluorination of pyridines bearing alkyl, halogen, ester, or ketone functions has been employed to prepare the corresponding 2-fluoro-substituted pyridines.