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pyrazine

Product name pyrazine
GOST no data
CAS 290-37-9

Pyrazine is a colorless crystalline solid. It is readily soluble in water, boundedly soluble in ethyl alcohol, diethyl ether, acetone. Pyrazine molecule has a planar geometry; C-C and C-H bond lengths are close to ones in benzene. C-N bond lengths are 0.134 nm.

Pyrazine basicity is slightly lower than pyridine one. Like other amines it can form salts with mineral and carboxylic acids. It is a heteroaromatic compound and it undergoes both electrophilic and nucleophilic aromatic substitution. Thus, it reacts with sodium amide NaNH2 in liquid ammonia resulting in 2-aminopyrazine. Also pyrazine can be oxidized with hydrogen peroxide to form N-oxides on one or both nitrogen atoms:

N-oxides of pyrazine formation


N-oxides are used for derivatizing pyrazine. N-oxide readily interacts with phosphorus oxytrichloride POCl3 to form 2-chloropyrazine-1-oxide, which is converted into 2-hydroxypyrazine-1-oxide by action of diluted sodium hydroxide NaOH water solution. Then N-oxide function is easily removed by reduction.

Pyrazine and its derivatives possess herbicide and antibiotic activity. Some biochemical compounds in nature have this sort of pyrazine section in their structures, such as pheromones. Alkylpyrazines are component of flavour of fried meat, potatoes, coffee, cocoa and some cheese.

Production.

Pyrazine is manufactured commercially:

  • by condensation of glyoxal with ethylene diamine at high temperature on copper-chromium oxide catalyst:

    Pyrazine synthesis


    Alkyl substituted pyrazine derivatives are prepared in similar procedure using substituted ethylene diamines and 1,2-dicarbonyl compounds.
  • by catalytic dehydrogenation of piperazine;

    Uses.

  • Pyrazine and its derivatives are widely used in pharmaceutical industry in antibiotics (e.g. aspergillic acid), antibacterial (pyrazine amide - antituberculous drug), antitumor, anticancer, diuretic drugs syntheses;
  • as an intermediate in azine dyes preparation;

  • Manufacturer(s) no data
    Chemical structure of pyrazine

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