Pyrazine

Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C4H4N2. It is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. It is a "deliquescent crystal or wax-like solid with a pungent, sweet, corn-like, nutty odour".[3]

Pyrazine
Pyrazine molecule
Pyrazine molecule
Names
Preferred IUPAC name
Pyrazine[1]
Other names
1,4-Diazabenzene, p-Diazine, 1,4-Diazine, Paradiazine, Piazine, UN 1325
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.480
EC Number
  • 206-027-6
UNII
  • InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H checkY
    Key: KYQCOXFCLRTKLS-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N2/c1-2-6-4-3-5-1/h1-4H
  • c1cnccn1
Properties
C4H4N2
Molar mass 80.09 g/mol
Appearance White crystals
Density 1.031 g/cm3
Melting point 52 °C (126 °F; 325 K)
Boiling point 115 °C (239 °F; 388 K)
Soluble
Acidity (pKa) 0.37[2] (protonated pyrazine)
-37.6·10−6 cm3/mol
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H228, H315, H319, H335
P210, P261, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
2
0
Flash point 55 °C (131 °F; 328 K) c.c.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.[4]

Synthesis

Many methods exist for the organic synthesis of pyrazine and its derivatives. Some of these are among the oldest synthesis reactions still in use.

In the Staedel–Rugheimer pyrazine synthesis (1876), 2-chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine.[5] A variation is the Gutknecht pyrazine synthesis (1879) also based on this selfcondensation, but differing in the way the alpha-ketoamine is synthesised.[6][7]

Gutknecht pyrazine synthesis

The Gastaldi synthesis (1921) is another variation:[8][9]

Gastaldi synthesis

See also

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 141. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
  3. "Pyrazine | C4H4N2 | ChemSpider". www.chemspider.com. Retrieved 4 January 2022.
  4. Zhang, Zhaohui (2003). "Tetramethylpyrazine scavenges superoxide anion and decreases nitric oxide production in human polymorphonuclear leukocytes". Life Sciences. 72 (22): 2465–2472. doi:10.1016/S0024-3205(03)00139-5. PMID 12650854.
  5. Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol (pp. 563–564) W. Staedel, L. Rügheimer doi:10.1002/cber.187600901174 Berichte der deutschen chemischen Gesellschaft Volume 9, Issue 1, pp. 563–564, 1876
  6. Mittheilungen Ueber Nitrosoäthylmethylketon H. Gutknecht Berichte der deutschen chemischen Gesellschaft Volume 12, Issue 2 , pp. 2290–2292, 1879 doi:10.1002/cber.187901202284
  7. Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01421-2
  8. G. Gastaldi, Gazz. Chim. Ital. 51, (1921) 233
  9. Amines: Synthesis, Properties and Applications Stephen A. Lawrence 2004 Cambridge University Press ISBN 0-521-78284-8
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