Quinoxaline

Quinoxaline Basic information
Product Name:Quinoxaline
Synonyms:1,4-Benxodiazine;1,4-Naphthyridine;Phenopiazine;Phenpiazine;Quinazine;USAF EK-7094;usafek-7094;QUINOXALINE
CAS:91-19-0
MF:C8H6N2
MW:130.15
EINECS:202-047-4
Product Categories:Building Blocks;Chemical Synthesis;Quinolines, Quinazolines and derivatives;Benzenes;Heterocyclic Building Blocks;Quinoxalines;Heterocyclic Compounds
Mol File:91-19-0.mol
Quinoxaline Structure
Quinoxaline Chemical Properties
Melting point 29-32 °C (lit.)
Boiling point 220-223 °C (lit.)
density 1.124 g/mL at 25 °C (lit.)
refractive index nD48 1.6231
Fp 209 °F
storage temp. 2-8°C
solubility alcohol: freely soluble(lit.)
pka0.56(at 20℃)
form Crystalline Low Melting Solid
color Light yellow to brown
Water Solubility SOLUBLE
Merck 14,8078
BRN 109351
Stability:Light Sensitive
LogP1.320
CAS DataBase Reference91-19-0(CAS DataBase Reference)
NIST Chemistry ReferenceQuinoxaline(91-19-0)
EPA Substance Registry SystemQuinoxaline (91-19-0)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-36/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS VD1225000
Hazard Note Irritant
TSCA Yes
HS Code 29339990
MSDS Information
ProviderLanguage
QuinoxalineEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
Quinoxaline Usage And Synthesis
Chemical Propertieslight yellow to brown crystalline
UsesOrganic synthesis.
UsesQuinoxaline is a reagent used in the synthesis of quinoxaline diimides as small molecule non-fullerene acceptors for organic solar cells.
DefinitionChEBI: A naphthyridine in which the nitrogens are at positions 1 and 4.
Synthesis Reference(s)Journal of the American Chemical Society, 69, p. 795, 1947 DOI: 10.1021/ja01196a015
The Journal of Organic Chemistry, 55, p. 1744, 1990 DOI: 10.1021/jo00293a014
Organic Syntheses, Coll. Vol. 4, p. 824, 1963
General DescriptionTransition metal-free acylation of quinoxaline derivatives, by cross dehydrogenative coupling (CDC) reaction, were studied.
Purification MethodsCrystallise quinoxaline from pet ether. It crystallises as the monohydrate on addition of water to a pet ether solution. It has UV: at 242 and 331nm (Ho –2); 234 and 316nm (pH 7.1). The picrate has m 161-162o.[Albert & Phillips J Chem Soc 1294 1956, Beilstein 23 H 176, 23 II 177, 23 III/IV 1226, 23/7 V 135.]
Quinoxaline Preparation Products And Raw materials
Raw materialsSodium bisulfite–>o-Phenylenediamine–>Glyoxal–>QUINOXALINE, 6-BROMO-1,2,3,4-TETRAHYDRO-–>5,8-DibroMoquinoxaline–>5-Bromoquinoxaline
Preparation ProductsOlaquindox–>2,3-Pyrazinedicarboxylic acid–>2,3-Pyrazinecarboxylic anhydride–>1,2,3,4-TETRAHYDRO-QUINOXALINE–>6-Bromoquinoxaline

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