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quinoxaline
Sign in to saveAlso known as 1,4-naphthyridine, benzoparadiazine, 1,4-diazanaphthalene, 1,4-benzodiazine, benzo[a]pyrazine, benzopyrazine
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. 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.
Chemical data
- Formula
- C8H6N2
- Molecular weight
- 130.15 g/mol
- IUPAC name
- quinoxaline
- SMILES
- C1=CC=C2C(=C1)N=CC=N2
- InChIKey
- XSCHRSMBECNVNS-UHFFFAOYSA-N
- XLogP
- 1.3
- Polar surface area
- 25.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 130.053
Show 4 more facts
- chemical formula
- C₈H₆N₂
- Commons category
- Quinoxaline
- canonical SMILES
- C1=CC=C2C(=C1)N=CC=N2
- melting point
- 30
via Wikidata · CC0
~1 min read
Article
3 sectionsContents
- Synthesis
- Uses
- References
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. 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. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB):