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== Pyrazine ==
{{Short description|Chemical compound}}
{{Chembox
| verifiedfields = changed
| verifiedrevid = 477241870
| Name = Pyrazine
| ImageFile = Pyrazine.png
| ImageSize = 120px
| IUPACName = Pyrazine
| OtherNames = 1,4-Diazabenzene
| Section1 = {{Chembox Identifiers
  | CASNo = 290-37-9
  | PubChem = 9261
  | ChemSpiderID = 8903
  | UNII = 0U46U6E8UK
  | InChI = 1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
  | InChIKey = KYQCOXFCLRTKLS-UHFFFAOYSA-N
  | SMILES = C1=CN=CC=N1
}}
| Section2 = {{Chembox Properties
  | C = 4
  | H = 4
  | N = 2
  | Appearance = Colorless solid
  | Density = 1.031 g/cm³
  | MeltingPt = 52 °C
  | BoilingPt = 115 °C
}}
}}


Pyrazine is a heterocyclic organic compound with the chemical formula C4H4N2. It is a six-membered aromatic ring with two nitrogen atoms at positions 1 and 4. Pyrazine is commonly used in the pharmaceutical and food industries due to its unique properties and versatile applications.
'''Pyrazine''' is a heterocyclic aromatic organic compound with the chemical formula C₄H₄N₂. It is a symmetrical molecule containing a six-membered ring with two nitrogen atoms at opposite positions in the ring. Pyrazine is a colorless solid with a melting point of 52 °C and a boiling point of 115 °C.


=== History ===
==Structure and Properties==
Pyrazine is part of the [[azine]] family, which includes other nitrogen-containing heterocycles such as [[pyridine]] and [[pyrimidine]]. The presence of nitrogen atoms in the ring structure contributes to its basicity and ability to participate in hydrogen bonding. Pyrazine is less basic than pyridine due to the electron-withdrawing effect of the second nitrogen atom.


Pyrazine was first synthesized in 1876 by the German chemist Wilhelm Knop. He obtained it by heating a mixture of glyoxal and ammonia. Since then, pyrazine has been extensively studied and its various derivatives have been synthesized for different purposes.
==Synthesis==
Pyrazine can be synthesized through several methods. One common method is the Gutknecht synthesis, which involves the condensation of [[glyoxal]] with [[ammonia]].


=== Properties ===
[[File:Gutknecht_Pyrazine_Synthesis.svg|Gutknecht Pyrazine Synthesis|thumb|right]]


Pyrazine is a colorless liquid with a distinct odor. It has a boiling point of 115 °C and a melting point of -37 °C. It is soluble in water and most organic solvents. Pyrazine exhibits aromatic properties due to the delocalization of electrons within its ring structure.
Another method is the Gastaldi synthesis, which involves the reaction of [[2,3-diaminopyridine]] with [[formic acid]].


=== Synthesis ===
[[File:GastaldiSynthesis.svg|Gastaldi Synthesis|thumb|left]]


Pyrazine can be synthesized through various methods. One common method involves the reaction of 1,4-diketones with hydrazine. Another method is the condensation of α,β-unsaturated carbonyl compounds with hydrazine. These reactions result in the formation of pyrazine derivatives with different substituents.
==Applications==
Pyrazine and its derivatives are used in a variety of applications. They are important in the flavor and fragrance industry due to their nutty and roasted aromas. Pyrazine derivatives are also used in pharmaceuticals, agrochemicals, and as intermediates in organic synthesis.


=== Applications ===
==Biological Significance==
 
Pyrazine compounds are found in nature and are known to be part of the aroma profile of many foods, including coffee, chocolate, and roasted nuts. They are also produced by certain bacteria and fungi, contributing to the flavor of fermented products.
Pyrazine and its derivatives have a wide range of applications in different industries:
 
1. Pharmaceutical Industry: Pyrazine derivatives have shown potential as antitumor, antimicrobial, and antiviral agents. They are used in the development of drugs for various diseases.
 
2. Food Industry: Pyrazine compounds are responsible for the characteristic flavors and aromas of many foods. They are used as flavoring agents in beverages, baked goods, and savory products.
 
3. Agriculture: Pyrazine derivatives have insecticidal properties and are used as pesticides to control pests in crops.
 
4. Material Science: Pyrazine-based compounds have been studied for their electronic and optical properties. They have potential applications in organic electronics and optoelectronic devices.
 
=== Safety ===
 
Pyrazine is generally considered safe for use in food and pharmaceutical applications. However, like any chemical compound, it should be handled with care and in accordance with safety guidelines. It is important to follow proper storage, handling, and disposal procedures to minimize any potential risks.
 
== See Also ==


==Related Pages==
* [[Pyridine]]
* [[Pyrimidine]]
* [[Heterocyclic compound]]
* [[Heterocyclic compound]]
* [[Aromaticity]]
* [[Flavoring agent]]
* [[Pesticide]]
== References ==
1. Knop, W. (1876). "Ueber die Einwirkung von Ammoniak auf Glyoxal". Justus Liebigs Annalen der Chemie. 180 (2): 257–263.
2. Katritzky, A. R.; Rees, C. W. (1996). Comprehensive Heterocyclic Chemistry II. Pergamon Press.
3. Zhang, Y.; et al. (2017). "Pyrazine derivatives: Synthesis, biological activities and structure-activity relationships". European Journal of Medicinal Chemistry. 125: 464–482.
4. Song, Y.; et al. (2019). "Pyrazine-based materials for organic electronics and optoelectronic devices". Journal of Materials Chemistry C. 7 (6): 1533–1550.
{{dictionary-stub1}}


== Pyrazine ==
[[Category:Pyrazines]]
<gallery>
[[Category:Heterocyclic compounds]]
File:Gutknecht_Pyrazine_Synthesis.svg|Gutknecht Pyrazine Synthesis
[[Category:Aromatic compounds]]
File:GastaldiSynthesis.svg|Gastaldi Synthesis
</gallery>

Latest revision as of 11:30, 23 March 2025

Chemical compound


Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C₄H₄N₂. It is a symmetrical molecule containing a six-membered ring with two nitrogen atoms at opposite positions in the ring. Pyrazine is a colorless solid with a melting point of 52 °C and a boiling point of 115 °C.

Structure and Properties[edit]

Pyrazine is part of the azine family, which includes other nitrogen-containing heterocycles such as pyridine and pyrimidine. The presence of nitrogen atoms in the ring structure contributes to its basicity and ability to participate in hydrogen bonding. Pyrazine is less basic than pyridine due to the electron-withdrawing effect of the second nitrogen atom.

Synthesis[edit]

Pyrazine can be synthesized through several methods. One common method is the Gutknecht synthesis, which involves the condensation of glyoxal with ammonia.

Gutknecht Pyrazine Synthesis

Another method is the Gastaldi synthesis, which involves the reaction of 2,3-diaminopyridine with formic acid.

Gastaldi Synthesis

Applications[edit]

Pyrazine and its derivatives are used in a variety of applications. They are important in the flavor and fragrance industry due to their nutty and roasted aromas. Pyrazine derivatives are also used in pharmaceuticals, agrochemicals, and as intermediates in organic synthesis.

Biological Significance[edit]

Pyrazine compounds are found in nature and are known to be part of the aroma profile of many foods, including coffee, chocolate, and roasted nuts. They are also produced by certain bacteria and fungi, contributing to the flavor of fermented products.

Related Pages[edit]

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