2423-65-6

Basic information

• Product Name: PYRAZINE N-OXIDE
• Synonyms: RARECHEM BG FB 0041;PYRAZINE N-OXIDE;Pyrazine-1-oxide;Pyrazine N-oxide 97%;1-oxidopyrazin-1-ium
• CAS NO: 2423-65-6
• Molecular Formula: C₄H₄N₂O
• Molecular Weight: 96.09
• Mol File: 2423-65-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 112-116 °C
• Boiling Point: 337.8 °C at 760 mmHg
• Flash Point: 158.1 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 0.000201mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.45±0.39(Predicted)
• CAS DataBase Reference: PYRAZINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRAZINE N-OXIDE(2423-65-6)
• EPA Substance Registry System: PYRAZINE N-OXIDE(2423-65-6)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 2423-65-6(Hazardous Substances Data)

Usage

Purification Methods

If the sample contains pyrazine-1-oxide, then place it in a Soxhlet extractor and extract it with hot pet ether (b 60-68o) in which the mono-oxide is soluble. Collect the dioxide from the thimble and recrystallise it from MeOH. It is dried in vacuo. It has at 1270cm-1 . [Koelsch & Gumprecht J Org Chem 23 1605 1958.]

InChI:InChI=1/C4H4N2O/c7-6-3-1-5-2-4-6/h1-4H

Upstream product

• 290-37-9 1,4-pyrazine 

Downstream Products

• 19847-12-2 2-pyrazine carbonitrile 
• 147032-16-4 2-(4-Methoxybenzylthio)pyrazine 
• 14508-49-7 2-chloropyrazin 
• 5049-61-6 2-Aminopyrazine 
• 922525-03-9 2-(4-methoxyphenyl)pyrazine 1-oxide 
• 85670-20-8 (E)-2-(α-Styryl)pyrazine 1-Oxide 
• 922524-99-0 2-p-tolylpyrazine 1-oxide 
• 58861-89-5 2-phenylpyrazine N⁽¹⁾-oxide 
• 1203590-24-2 3-biphenyl-4-yl-4-hydroxy-piperazine-1-carboxylic acid tert-butyl ester 
• 1203590-25-3 3-biphenyl-2-yl-4-hydroxy-piperazine-1-carboxylic acid tert-butyl ester 
• 1203590-16-2 4-hydroxy-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Green Oxidation Process in the Synthesis of LLM-105 with H2O2/Peroxotungstate System and its Theoretical Study

A new catalytic system was developed and applied to the oxidation reactions involved in the synthesis of LLM-105, in which protonated peroxotungstate combining chitosan was used as catalyst. With H2O2as oxidant, good to excellent yields could be achieved in the synthesis of pyrazine-1-oxide, 2,6-dimethoxypyrazine-1-oxide, 2,6-dichloropyrazine-1-oxide, and 2-chloro-6-methoxypyrazine-1-oxide without any addition of trifluoracetic acid, which provided a significant exploration toward novel and environmentally benign synthetic route for LLM-105. Theoretical studies were also carried out with Gaussian 03 to evaluate the oxidation process. All of the calculated data matched well with our experimental results.

A Biocatalytic Synthesis of Heteroaromatic N-Oxides by Whole Cells of Escherichia coli Expressing the Multicomponent, Soluble Di-Iron Monooxygenase (SDIMO) PmlABCDEF

Aromatic N-oxides (ArN?OX) are desirable biologically active compounds with a potential for application in pharmacy and agriculture industries. As biocatalysis is making a great impact in organic synthesis, there is still a lack of efficient and convenient enzyme-based techniques for the production of aromatic N-oxides. In this study, a recombinant soluble di-iron monooxygenase (SDIMO) PmlABCDEF overexpressed in Escherichia coli was showed to produce various aromatic N-oxides. Out of 98 tested N-heterocycles, seventy were converted to the corresponding N-oxides without any side oxidation products. This whole-cell biocatalyst showed a high activity towards pyridines, pyrazines, and pyrimidines. It was also capable of oxidizing bulky N-heterocycles with two or even three aromatic rings. Being entirely biocatalytic, our approach provides an environmentally friendly and mild method for the production of aromatic N-oxides avoiding the use of strong oxidants, organometallic catalysts, undesirable solvents, or other environment unfriendly reagents. (Figure presented.).

Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N -Oxides

A Pd-catalyzed direct C2-alkenylation of azine N-oxides with allyl acetate is disclosed. The products are formed through an allylation/isomerization cascade process. The use of a tri-tert-butylphosphonium salt as the ligand precursor and KF is mandatory for optimal yields. When cinnamyl acetate is used, the same catalytic system promotes C2-cinnamylation of the azine N-oxide without subsequent isomerization. A mechanism is proposed on the basis of experimental studies and DFT calculations.