2-Fluoropyridine

Base Information

• Chemical Name: 2-Fluoropyridine
• CAS No.: 372-48-5
• Molecular Formula: C5H4FN
• Molecular Weight: 97.0919
• Hs Code.: 29333999
• European Community (EC) Number: 206-757-5
• NSC Number: 5077
• UNII: WKQ4JPY48S
• DSSTox Substance ID: DTXSID70190689
• Nikkaji Number: J43D
• Wikidata: Q72476692
• ChEMBL ID: CHEMBL1162360
• Mol file: 372-48-5.mol

Synonyms:2-fluoropyridine

Chemical Property of 2-Fluoropyridine

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 14.4mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 125.929 °C at 760 mmHg
• PKA: -0.44(at 25℃)
• Flash Point: 28.333 °C
• PSA: 12.89000
• Density: 1.118 g/cm³
• LogP: 1.22070
• Storage Temp.: Flammables area
• Water Solubility.: Soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 97.032777294
• Heavy Atom Count: 7
• Complexity: 56

Purity/Quality:

99% ^*data from raw suppliers

2-Fluoropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F, Xn
• Hazard Codes: Xi,F,Xn
• Statements: 10-36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)F
• Uses: 2-Fluoropyridine is a useful precursor of 2,3-disubstituted pyridines which is made by the possibility of metallation at C-3, together with the ready nucleophilic displacement of the activated fluorine. It can also react with thiophene to get 2-thiophen-2-yl-pyridine. It is used in the synthesis of aminopyridines.

Technology Process of 2-Fluoropyridine

There total 75 articles about 2-Fluoropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 33.0%

N-fluoropyridinium triflate (107263-95-6) → 2-phenylpyridine (1008-89-5) + pyridin-2-yl trifluoromethanesulfonate (65007-00-3) + 2-fluoropyridine (372-48-5)

Guidance literature:

With triethylamine; In benzene; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)96186-0

Reference yield: 32.0%

pyridine (110-86-1) → 2,6-difluoro pyridine (1513-65-1) + 2-fluoropyridine (372-48-5)

Guidance literature:

With co-precipitated copper aluminum fluoride (CuAl₀₁); at 500 ℃; Gas phase; Inert atmosphere;

Reference yield:

pyridine (110-86-1) + carbon tetrafluoride (75-73-0) → 3-Fluoropyridine (372-47-4) + 4-fluoropyridine (694-52-0) + fluorobenzene (462-06-6) + 2-fluoropyridine (372-48-5)

Guidance literature:

at -196.1 ℃; Product distribution; Mechanism; var. aromatics;

upstream raw materials:

pyridine

2-aminopyridine

tetrahydrofuran

N-fluoropyridinium triflate

Downstream raw materials:

2-fluoro-3-(phenyl-1-hydroxymethyl)pyridine

2-F-pyridineH⁺

1,1-bis(methylthio)ethylene

1-(2-Fluoro-3-pyridyl)ethanol

Refernces

Promoting effect of ionic liquids on ligand substitution reactions

10.1016/j.jorganchem.2005.02.018

The research investigates how ionic liquid solvents influence ligand substitution reactions, specifically focusing on the displacement of anionic ligands by pyridine derivatives in trans-(Ph3P)2Rh(CO)NO3. The study aims to understand the effects of ionic liquids on reaction rates, mechanisms, and selectivity, particularly in the context of homogeneous catalytic processes. 1-butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6]) plays a crucial role as a solvent medium for studying ligand substitution reactions. Specifically, it is used to investigate how ionic liquids can influence the displacement of anionic ligands by neutral molecules in the complex trans-(Ph3P)2Rh(CO)NO3. Key chemicals used include various pyridine derivatives such as 2-fluoropyridine and 2,6-difluoropyridine. The researchers found that these ionic liquids significantly promote the formation of charge-separated ligand substitution products compared to dichloromethane, with [C4mim][PF6] showing a stronger effect than [C6pyr][Tf2N]. The study concludes that ionic liquids can enhance catalytic processes where anionic ligands compete for coordination to the active site, and their weak coordinating ability makes them suitable alternatives to traditional polar organic solvents in such reactions.

Cross-Coupling of Secondary Amides with Tertiary Amides: The Use of Tertiary Amides as Surrogates of Alkyl Carbanions for Ketone Synthesis

10.1002/cjoc.201900215

The research aims to provide a novel method for the synthesis of ketones through the cross-coupling of secondary amides with tertiary amides under mild conditions. The study concludes that tertiary amides can effectively act as surrogates for alkyl carbanions, leading to the successful synthesis of ketones while demonstrating excellent chemoselectivity and functional group tolerance. Key chemicals used in the process include Vaska's catalyst for the partial reduction of tertiary amides to enamines, trifluoromethanesulfonic anhydride (Tf2O) for the in situ generation of nitrilium ions from secondary amides, and 2-fluoropyridine as a reagent.