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

Description

3-chloro-1-oxido-pyrazine, a chlorinated derivative of the heterocyclic aromatic organic compound pyrazine, is characterized by its molecular formula C4H3ClN2O. The incorporation of a chlorine atom and a nitrogen oxide group endows this compound with unique chemical properties, making it a versatile building block in organic synthesis and industrial processes.

Uses

Used in Pharmaceutical Industry:
3-chloro-1-oxido-pyrazine is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse molecular entities with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-chloro-1-oxido-pyrazine serves as a key intermediate in the production of pesticides and other agrochemicals. Its reactivity and functional groups facilitate the synthesis of compounds with specific pesticidal or herbicidal activities, enhancing crop protection and yield.
Used in Flavor and Fragrance Industry:
3-chloro-1-oxido-pyrazine is employed as a key building block in the creation of specific aroma compounds in the flavor and fragrance industry. Its unique chemical properties enable the development of novel fragrances and flavorings, adding to the diversity and complexity of scents and tastes in various consumer products.

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

• 770-00-3 methylester of pyrazinecarboxylic acid 4-oxide 
• 55557-52-3 2-chloro-3-cyanopyrazine 
• 14508-49-7 2-chloropyrazin 
• 19745-07-4 2,5-dichloropyrazine 
• 4858-85-9 2,3-dichloropyrazine 
• 4774-14-5 2,6-dichloropyrazine 
• 3735-46-4 1,2-dihydro-2-oxo-pyrazine 4-oxide 
• 136742-98-8 2-benzylthiopyrazine 4-oxide 
• 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 
• 147032-17-5 2-Chloro-3-(4-methoxybenzylthio)pyrazine 

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