372-47-4

Basic information

• Product Name: 3-Fluoropyridine
• Synonyms: Pyridine, 3-fluoro-;3-FLUOROPYRIDINE;3-Fluoroypyridine;3-FLUOROPYRIDINE 98% (GC);3-Fluoropyridine,98%;3-Fluoropyridine 98%;3-Fluoropyridine,99%;3-Fluoropyridine, 99% 1GR
• CAS NO: 372-47-4
• Molecular Formula: C5H4FN
• Molecular Weight: 97.09
• EINECS: 206-755-4
• Product Categories: Fluorin-contained pyridine series;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Halides;Pyridines;Pyridines derivates;Fluoropyridines;Halopyridines;C5;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Fluorine series;alkyl Fluorine
• Mol File: 372-47-4.mol

Chemical Properties

• Melting Point: 251-254°C (dec.)
• Boiling Point: 107-108 °C(lit.)
• Flash Point: 56 °F
• Appearance: Clear yellow/Liquid
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 31.6mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: Flammables area
• PKA: pK1:2.97(＋1) (25°C)
• BRN: 105702
• CAS DataBase Reference: 3-Fluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoropyridine(372-47-4)
• EPA Substance Registry System: 3-Fluoropyridine(372-47-4)

Safety Data

• Hazard Codes: F,Xi,Xn
• Statements: 11-36/37/38-20/21/22
• Safety Statements: 16-26-36/37/39-33-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 372-47-4(Hazardous Substances Data)

Usage

Chemical Properties

clear, colorless to yellow liquid.

Uses

3-Fluoropyridine was used in the synthesis of 3-halopyridin-4-yl-boronic acids and esters.

Preparation

A combination of CsF and HF provides a very reactive fluoride source and has shown faint promise with 3-chloropyridine giving 3-fluoropyridine in a very low yield.

General Description

3-Fluoropyridine is oxidized to corresponding N-oxides, which on treatment with hot acetic anhydride and hydrolysis yields 3-halo-2-pyridones. Microwave spectrum of 3-fluoropyridine has been investigated in the frequency range of 8-18GHz at dry ice temperature. Deprotonation of 3-fluoropyridine with Bu3MgLi in THF at -10°C has been studied.

InChI:InChI=1/C5H4FN/c6-5-2-1-3-7-4-5/h1-4H

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 695-37-4 3-fluoropyridine-1-oxide 
• 59278-67-0 2-fluoropyridine-H⁽¹⁺⁾ 
• 3619-02-1 (S)-N-acetylalanine methyl ester 
• 2546-52-3 bromo-4 fluoro-3 pyridine 
• 40273-45-8 2-bromo-3-fluoropyridine 
• 96-22-0 pentan-3-one 
• 206991-13-1 C₂₁H₃₂N₂O₃ 
• 700-16-3 Pentafluoropyridine 
• 110-86-1 pyridine 
• 75-73-0 carbon tetrafluoride 
• 89959-08-0 MoO(2,6-bis(2,2-diphenyl-2-mercaptoethyl)pyridine^(2-))(DMF) 
• 1692-25-7 3-pyridylboronic acid 
• 393-53-3 3-fluoroisonicotinic acid 

Downstream Products

• 366-65-4 3-fluoro-1-(4-fluoro-phenacyl)-pyridinium; bromide 
• 695-37-4 3-fluoropyridine-1-oxide 
• 77332-77-5 3-fluoro-4-(trimethylsilyl)pyridine 
• 87674-09-7 3-fluoro-2-(trimethylsilyl)pyridine 
• 87674-19-9 2,4-di-trimethylsilyl-3-fluoropyridine 
• 151-56-4 ethyleneimine 
• 59278-67-0 2-fluoropyridine-H⁽¹⁺⁾ 
• 87-85-4 hexamethylbenzene radical cation 
• 2267-37-0 acetic acid-(3-fluoro-[2]pyridyl ester) 
• 17282-04-1 2-chloro-3-fluoropyridine 
• 5005-40-3 α-phenyl-3-pyridineacetonitrile 
• 104642-45-7 C₉H₁₂O₃S*C₅H₅FN₂ 
• 87674-14-4 2-(1-hydroxyethyl)-3-fluoropyridine 
• 87674-15-5 4-(1-hydroxyethyl)-3-fluoropyridine 

Relevant articles and documents

Photorelease of Pyridines Using a Metal-Free Photoremovable Protecting Group

The photorelease of bioactive molecules has emerged as a valuable tool in biochemistry. Nevertheless, many important bioactive molecules, such as pyridine derivatives, cannot benefit from currently available organic photoremovable protecting groups (PPGs). We found that the inefficient photorelease of pyridines is attributed to intramolecular photoinduced electron transfer (PET) from PPGs to pyridinium ions. To alleviate PET, we rationally designed a strategy to drive the excited state of PPG from S1 to T1 with a heavy atom, and synthesized a new PPG by substitution of the H atom at the 3-position of 7-dietheylamino-coumarin-4-methyl (DEACM) with Br or I. This resulted in an improved photolytic efficiency of the pyridinium ion by hundreds-fold in aqueous solution. The PPG can be applied to various pyridine derivatives. The successful photorelease of a microtubule inhibitor, indibulin, in living cells was demonstrated for the potential application of this strategy in biochemical research.

Selective fluorination of pyridine and its derivatives in the presence of high-oxidation-state transition metals

The oxidative fluorination of pyridine and 4-ethylpyridine under chemical and electro-chemical conditions in the presence of transition metal (high-oxidation-state nickel, cobalt, and silver) salts was studied. The chemical fluorination affords 2-fluoropyridine in all cases, while the electrochemical fluorination results in 2-fluoroor 3-fluoropyridine depending on the catalyst used.

Mild fluorination of chloropyridines with in situ generated anhydrous tetrabutylammonium fluoride

This paper describes the fluorination of nitrogen heterocycles using anhydrous NBu4F. Quinoline derivatives as well as a number of 3- and 5-substituted pyridines undergo high-yielding fluorination at room temperature using this reagent. These results with anhydrous NBu4F compare favorably to traditional halex fluorinations using alkali metal fluorides, which generally require temperatures of ≥100 °C.

Catalytic hydrodefluorination of fluoroaromatics with silanes as hydrogen source at a binuclear rhodium complex: Characterization of key intermediates

Stoichiometric and catalytic hydrodefluorination reactions of fluorinated aromatic substrates on using [Rh(μ-H)(dippp)]2 (1) (dippp = 1,3-bis(diisopropylphosphino)propane) as catalyst and HSiEt3 as a hydrogen source are reported. Treatment of the hydrido complex 1 with the fluoroarenes gave the fluorido complex [Rh(μ-F)(dippp)]2 (2) and organic hydrodefluorination products. An unusual ortho-selectivity was observed in the reaction of 2,3,5,6-tetrafluoropyridine and pentafluorobenzene giving the 1,2-hydrodefluorinated products. The binuclear structure of complex 2 in the solid state was confirmed by X-ray diffraction. The fluorido complex 2 reacted with HSiEt3 and HSiiPr3 by elimination of the corresponding fluorosilanes to afford the η2-silane hydrido complexes [Rh(H)(η2-HSiEt3)(dippp)] (3) and [Rh(H)(η2-HSiiPr3)(dippp)] (4), respectively. The structures of the complexes 3 and 4 were derived from NMR data and DFT calculations. Catalytic reactions of pentafluoropyridine, 2,3,5,6-tetrafluoro- pyridine or 2,3,5,6-tetra-fluoropyridine, hexa- and pentafluorobenzene with HSiEt3 in the presence of 5 mol% of 1 afforded hydrodefluorination products with up to 19 turnovers after 48 h at 50 C. In contrast to the stoichiometric reactions, the catalytic transformations resulted predominantly in hydrodefluorinations at the para-position of the nitrogen atom in the heterocycles giving evidence for two different C-F activation pathways. Compound 3 can be considered to be an intermediate in the catalytic hydrodefluorinations of the fluoroarenes.

An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates

The stable Pd(0) species [(1,5-cyclooctadiene)(L·Pd)2] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

FLUORINATION OF ORGANIC COMPOUNDS

Methods for fluorinating organic compounds are described herein.

Deoxyfluorination of phenols

An operationally simple ipso fluorination of phenols with a new deoxyfluorination reagent is presented.

Efficient synthesis of aryl fluorides

Chemical Equation Presented Creating C-F bonds: A novel electrophilic fluorination of aryl and heteroaryl Crignard reagents has been discovered and was used for the efficient synthesis of various aryl fluoride derivatives (see picture; THF = tetrahydrofuran).

Silver-catalyzed protodecarboxylation of heteroaromatic carboxylic acids

[Chemical Equation Presented] A simple and highly efficient protodecarboxylation procedure for a variety of heteroaromatic carboxylic acids catalyzed by Ag2CO3 and AcOH in DMSO is described. This methodology can also perform the selective monoprotodecarboxylation of several aromatic dicarboxylic acids.

Fluorination of boronic acids mediated by silver(I) Triflate

A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters Is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.