6863-76-9

Basic information

• Product Name: 3-chloro-1-oxido-pyrazine
• Synonyms: 3-chloro-1-oxido-pyrazine;3-Chloro-1-pyrazinium-1-olate;3-Chloropyrazine 1-oxide
• CAS NO: 6863-76-9
• Molecular Formula: C₄H₃ClN₂O
• Molecular Weight: 130.53362
• Mol File: 6863-76-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 373.5 °C at 760 mmHg
• Flash Point: 179.7 °C
• Appearance: /
• Density: 1.44 g/cm³
• Vapor Pressure: 1.91E-05mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: 3-chloro-1-oxido-pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-1-oxido-pyrazine(6863-76-9)
• EPA Substance Registry System: 3-chloro-1-oxido-pyrazine(6863-76-9)

Safety Data

• Hazardous Substances Data: 6863-76-9(Hazardous Substances Data)

Usage

General Description

3-chloro-1-oxido-pyrazine is a chemical compound with the molecular formula C4H3ClN2O. It is a chlorinated derivative of pyrazine, which is a heterocyclic aromatic organic compound. The presence of the chlorine atom and the nitrogen oxide group make 3-chloro-1-oxido-pyrazine useful in various chemical reactions and synthetic processes. It is commonly used as an intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds. Additionally, it has applications in the flavor and fragrance industry, where it is used as a key building block for creating specific aroma compounds. The compound's unique chemical structure and properties make it an important and versatile building block in organic synthesis and industrial processes.

InChI:InChI=1/C4H3ClN2O/c5-4-3-7(8)2-1-6-4/h1-3H

Upstream product

• 14508-49-7 2-chloropyrazin 
• 6863-77-0 3-aminopyrazine 1-oxide 

Downstream Products

• 147032-17-5 2-Chloro-3-(4-methoxybenzylthio)pyrazine 
• 128455-83-4 3-(2-phenylethynyl)pyrazine 1-oxide 
• 128455-85-6 (Z)-3-(1-benzylidene-3-phenyl-2-propynyl)pyrazine 1-oxide 
• 128455-84-5 (E)-3-(2,4-diphenyl-1-buten-3-ynyl)pyrazine 1-oxide 
• 770-00-3 methylester of pyrazinecarboxylic acid 4-oxide 
• 55557-52-3 2-chloro-3-cyanopyrazine 
• 19745-07-4 2,5-dichloropyrazine 
• 4858-85-9 2,3-dichloropyrazine 
• 4774-14-5 2,6-dichloropyrazine 
• 14508-49-7 2-chloropyrazin 
• 3735-46-4 1,2-dihydro-2-oxo-pyrazine 4-oxide 
• 136742-98-8 2-benzylthiopyrazine 4-oxide 

Relevant articles and documents

Oxidation methods for aromatic diazines. Part II. Chlorinated pyrazine N-oxides

Chlorinated pyrazines are directly oxidized to the N-oxides using dimethyldioxirane. The reactions were found to be completely regioselective and the products were easily isolated in good yields. These oxidations were comparable to the conversion of methylated pyrazines to pyrazine monoxides and dioxides described by us in part 1. Oxidation with dimethyldioxirane in acetone overcomes problems associated with the isolation of hydrophilic pyrazine N-oxides obtained by using other oxidation reagents.

Emimycin and its nucleoside derivatives: Synthesis and antiviral activity

The synthesis of emimycin, 5-substituted emimycin analogues and the corresponding ribo- and 2′-deoxyribonucleoside derivatives is described. Emimycin, its 5-substituted congeners and the ribonucleoside derivatives are completely devoid of antiviral activity against RNA viruses. In contrast, some of the 2′-deoxyribosyl emimycin derivatives are potent inhibitors of the replication of herpes simplex virus-1 and varicella-zoster virus, lacking cytotoxicity.

Identification of 2-chloropyrazine oxidation products and several derivatives by multinuclear magnetic resonance

1H, 13C, 14N and 15N NMR chemical shifts were used to prove the structures of the products of 2-chloropyrazine oxidation. It was shown that oxidation by hydrogen peroxide in acetic acid or m-chloroperbenzoic acid leads to the N4-oxide, whereas potassium persulfate in sulfuric acid gives the N1-oxide as the main product. Additionally, the results of NMR measurements of products from the nucleophilic substitution of the chlorine atom by azide anion, yielding the respective azides, and ethylation reactions of both 2-chloropyrazine N-oxides leading to the N-ethyl salts confirm the structures of both isomeric N-oxides. Protonation studies of the compounds obtained are also reported. The favoured protonation site is found to be the N atom that is not hindered by any substituents, and in some cases probably the oxygen atom of the N-oxide function. Copyright