Quinoxaline

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Structural formula
Structural formula of quinoxaline
General
Surname Quinoxaline
other names
  • 1,4-benzodiazine
  • 1,4-diazanaphthalene
  • Benzopyrazine
Molecular formula C 8 H 6 N 2
Brief description

light yellow to brown solid with a characteristic odor

External identifiers / databases
CAS number 91-19-0
EC number 202-047-4
ECHA InfoCard 100,001,862
PubChem 7045
Wikidata Q419930
properties
Molar mass 130.15 g mol −1
Physical state

firmly

density

1.33 g cm −3 (20 ° C)

Melting point

29-34 ° C

boiling point

220-223 ° C

solubility

soluble in water, ethanol , diethyl ether and benzene

Refractive index

1.6231 (48 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Quinoxaline is an organic compound that belongs to the heterocycles (more precisely: heteroaromatics and diazanaphthalenes ). The compound consists of a benzene ring to which a pyrazine ring is fused . Quinoxaline is isomeric to cinnoline , quinazoline and phthalazine .

Extraction and presentation

Quinoxaline can be synthesized by the condensation of ortho- phenylenediamine with glyoxal .

Derivatives of quinoxaline can generally be obtained by condensation of 1,2-dicarbonyl compounds, e.g. B. Benzil or its derivatives are represented with derivatives of ortho- phenylenediamine.

Quinoxaline Synthesis

use

Quinoxaline forms the backbone of many compounds as dyes , drugs , antibiotics (eg. B. carbadox , echinomycin , Levomycin , Sulfaquinoxalin and Atinoleutin ) and the vulcanization may be used.

Web links

Individual evidence

  1. ↑ Quinoxaline data sheet from Acros, accessed on February 19, 2010.
  2. ↑ Quinoxaline data sheet from AlfaAesar, accessed on February 19, 2010 ( PDF )(JavaScript required) .
  3. ↑ a b Entry on quinoxaline at ChemBlink , accessed on February 19, 2010.
  4. ↑ a b c Entry on quinoxaline. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.
  5. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-454.
  6. ↑ a b Quinoxaline data sheet from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
  7. ^ A b D. J. Brown, EC Taylor: The Chemistry of Heterocyclic Compounds, Quinoxalines: Supplement II: 61 , p. 16, 1st edition, John Wiley & Sons, New York, 2004, ISBN 0-471-26495-4 .
  8. ↑ Beyer-Walter, Textbook of Organic Chemistry, 23rd Edition, S. Hirzel Verlag 1998 ISBN 3-7776-0808-4
  9. ↑ T. Otaka, S. Shoji, Y. Hamura, T. Funayama, German Patent DE102005055649A1, 2006.