Quinoxaline

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Names
Preferred IUPAC name

Quinoxaline[1]

Other names

Benzo[b]pyrazine, Benzopyrazine, Benzoparadiazine, 1,4-Benzodiazine, Phenopiazine, Phenpiazine, Quinazine, Chinoxalin

Identifiers

CAS Number

* 91-19-0 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:36616 Y

ChEMBL |

* ChEMBL39444 Y

ChemSpider |

* 21106470 Y

EC Number |

* 202-047-4

KEGG |

* C18575 Y

PubChem CID

* 7045

UNII |

* QM4AR6M6T8 Y

InChI

* InChI=1S/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H Y

Key: XSCHRSMBECNVNS-UHFFFAOYSA-N Y

* InChI=1/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H

Key: XSCHRSMBECNVNS-UHFFFAOYAS

SMILES

* c1cccc2nccnc12

Properties

Chemical formula

| C8H6N2
Molar mass | 130.150 g·mol−1
Melting point | 29-32 °C
Boiling point |  220 to 223 °C (428 to 433 °F; 493 to 496 K)
Acidity (pKa)  | 0.60[2]
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline.[3] It is a colorless oil that melts just above room temperature. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals (such as varenicline), and antibiotics such as olaquindox, carbadox, echinomycin, levomycin and actinoleutin.

## Synthesis

They can be formed by condensing ortho-diamines with 1,2-diketones. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene.[4] Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.[3] Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB):[5]

One study[6] used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene:

Quinoxaline Synthesis

## Uses

The antitumoral properties of quinoxaline compounds have been of interest.[7] Recently, quinoxaline and its analogs have been investigated as the catalyst's ligands.[8]

## 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. pp. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. ↑ Brown, H.C. (1955). Baude, E.A.. ed. Determination of Organic Structures by Physical Methods. New York: Academic Press.
3. ↑ 3.0 3.1 One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed (1911). "Quinoxalines". Encyclopædia Britannica. 22 (11th ed.). Cambridge University Press. p. 760.
4. ↑ 2,3-Pyrazinedicarboxylic Acid" Reuben G. Jones and Keith C. McLaughlin Org. Synth. 1950, 30, 86. doi:10.15227/orgsyn.030.0086. This paper describes the preparation of quinoxaline as an intermediate.
5. ↑ Xiang-Hong Wu et al. (2004). "Solution-phase reductive cyclization of 2-quinoxalinol analogs: Systematic study of parallel synthesis". Mol. Divers. 8 (2): 165–174. doi:10.1023/B:MODI.0000025639.89179.60. PMID 15209169.
6. ↑ Heravi, Majid M. (2006). "Facile synthesis of quinoxaline derivatives using o-iodoxybenzoic acid (IBX) at room temperature". Arkivoc 2006 (16): 16–22. doi:10.3998/ark.5550190.0007.g02.
7. ↑ Jean Renault et al. (1981). "Heterocyclic quinones.2.Quinoxaline-5,6-(and 5-8)-diones-Potential antitumoral agents". Eur. J. Med. Chem. 16 (6): 545–550.
8. ↑ Xianghong Wu; Anne E. V. Gorden (2007). "Regioselective Synthesis of Asymmetrically Substituted 2-Quinoxalinol Salen Ligands". J. Org. Chem. 72 (23): 8691–8699. doi:10.1021/jo701395w. PMID 17939720.

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*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …