2402-98-4

Basic information

• Product Name: pyridine-2-carbonitrile 1-oxide
• Synonyms: pyridine-2-carbonitrile 1-oxide;2-Pyridinecarbonitrile 1-oxide;1-oxidopyridin-1-ium-2-carbonitrile;2-carbonitrilepyridine 1-oxide
• CAS NO: 2402-98-4
• Molecular Formula: C₆H₄N₂O
• Molecular Weight: 120.10876
• EINECS: 219-286-5
• Mol File: 2402-98-4.mol

Chemical Properties

• Melting Point: 123-124 °C
• Boiling Point: 382.7°Cat760mmHg
• Flash Point: 185.3°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 4.63E-06mmHg at 25°C
• Refractive Index: 1.567
• PKA: -1.92±0.10(Predicted)
• CAS DataBase Reference: pyridine-2-carbonitrile 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: pyridine-2-carbonitrile 1-oxide(2402-98-4)
• EPA Substance Registry System: pyridine-2-carbonitrile 1-oxide(2402-98-4)

Safety Data

• Hazardous Substances Data: 2402-98-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Pyridine-2-carbonitrile 1-oxide serves as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for versatile chemical transformations, making it a valuable building block in the creation of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, pyridine-2-carbonitrile 1-oxide is utilized as a precursor for the development of novel therapeutic agents. Its ability to form diverse chemical entities contributes to the discovery of new drugs with potential medicinal properties.
Used in Agrochemical Industry:
Pyridine-2-carbonitrile 1-oxide also finds application in the agrochemical field, where it is employed in the synthesis of pesticides and other crop protection agents. Its reactivity and structural features enable the production of effective compounds designed to protect crops from pests and diseases.
Safety Precautions:
It is crucial to handle pyridine-2-carbonitrile 1-oxide with care, as it may possess hazardous properties. Proper safety measures should be implemented during its use to ensure controlled and secure processing, minimizing potential risks to both individuals and the environment.

InChI:InChI=1/C6H4N2O/c7-5-6-3-1-2-4-8(6)9/h1-4H

Upstream product

• 6974-72-7 2-pyridinecarboxamide 1-oxide 
• 1452-77-3 pyridine-2-carboxylic acid amide 
• 24145-26-4 (Z)-2-pyridinecarbaldehyde 1-oxide oxime 
• 100-70-9 2-Cyanopyridine 

Downstream Products

• 65370-37-8 2-(N'-hydroxycarbamimidoyl)pyridine 1-oxide 
• 1367127-60-3 C₂₀H₁₇FN₂O₄ 
• 1367127-58-9 C₂₀H₁₅FN₂O₃ 
• 1367127-56-7 C₂₀H₁₃FN₂O 
• 1127563-71-6 6-(4-(4-fluorophenoxy)phenyl)-4-chloropyridine-2-carbonitrile 
• 1367126-66-6 C₂₄H₂₃FN₄O₂ 
• 1367124-88-6 6-(4-(4-fluorophenoxy)phenyl)-4-((2-morpholinoethyl)amino)picolinamide 
• 1127562-03-1 C₁₃H₁₀N₂O 
• 1127561-99-2 C₁₅H₁₂N₂O₃ 
• 1127562-01-9 C₁₃H₁₀N₂O₂ 
• 1127563-68-1 6-(4-(4-fluorophenoxy)phenyl)pyridine-2-carbonitrile N-oxide 
• 65370-37-8 picolinic acid amidoxime N-oxide 
• 100-70-9 2-Cyanopyridine 
• 2893-33-6 pyridine-2,6-dinitrile 

Relevant articles and documents

Regioselective Three-Component Reaction of Pyridine N-Oxides, Acyl Chlorides, and Cyclic Ethers

A novel three-component reaction of pyridine N-oxides, acyl chlorides, and cyclic ethers is described. Treatment of an electron-deficient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25-50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic-labeling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

Catalyst-free and selective oxidation of pyridine derivatives and tertiary amines to corresponding N-oxides with 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane

The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields. Graphical abstract: The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields.

Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine: N -oxides

A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C-H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63-92%; 19 examples). In the cases of 3-substituted PyO, the C-H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.

Base free regioselective synthesis of α-triazolylazine derivatives

A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.

PYRIDINE COMPOUNDS AND THE USES THEREOF

The invention relates to substituted pyridine compounds of Formula (I) and the pharmaceutically acceptable salts, prodrugs, and solvates thereof, wherein R1a, A1, A2, E, G, Z1, and Z2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.

Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N -oxides

Chemical equations presented. Substituted bipyridines were efficiently prepared by direct coupling between pyridine N-oxides and halopyridines using a palladium catalyst. Pyridine N-oxides with electron-withdrawing substitutents gave the best yields. This method allows the convenient preparation of 2,2′-, 2,3′-, and 2,4′-bipyridines which are useful as functionalized ligands for metal complexes or as building blocks for supramolecular architectures.

Ruthenium catalyzed oxidation of tertiary nitrogen compounds with molecular oxygen: An easy access to N-oxides under mild conditions

A variety of tertiary nitrogen compounds have been efficiently oxidized to their corresponding N-oxides in excellent yields with molecular oxygen as a sole oxidant and ruthenium trichloride as catalyst.

Oxidation of tertiary nitrogen compounds to N-oxides by molecular oxygen-aldehyde system in the absence of metal catalyst

A variety of tertiary nitrogen compounds have been oxidized to corresponding N-oxides in near quantitative yields by molecular oxygen/2-methylpropanal system in the absence of metal catalyst.

An efficient synthesis of heterocyclic N-oxides over molecular sieve catalyst

Heterocyclic N-oxides have been synthesized in very high yields over redox molecular sieve catalysts in the presence of H2O2.