6-Aminoquinoxaline Chemical Properties

Melting point:

159 °C

Boiling point:

254.27°C (rough estimate)

Density 

1.2109 (rough estimate)

refractive index 

1.5400 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

2.57±0.30(Predicted)

color 

Yellow to Dark Yellow

InChI

InChI=1S/C8H7N3/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-5H,9H2

InChIKey

MSGRFBKVMUKEGZ-UHFFFAOYSA-N

SMILES

N1C2C(=CC(N)=CC=2)N=CC=1

CAS DataBase Reference

6298-37-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36/38-22

Safety Statements 

24/25-36/39-26

WGK Germany 

1

HazardClass 

IRRITANT

HS Code 

29339900

6-Aminoquinoxaline Usage And Synthesis

Chemical Properties

Yellow solid

Uses

6-Quinoxalinamine is used in the synthetic preparation and evaluation of novel nitroheterocyclic hypoxic markers for solid tumor.

Definition

ChEBI: 6-Quinoxalinamine is a quinoxaline derivative.

Synthesis

General procedure for the synthesis of 6-aminoquinoxaline from 6-nitroquinoxaline: 10% palladium carbon (50 mg) was added to a solution of 6-nitroquinoxaline (500 mg, 2.86 mmol) in methanol (20 mL) and the reaction mixture was stirred for 4 hr. under an atmosphere of hydrogen at 1 atm. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was evaporated to remove the solvent. The residue was purified by silica column chromatography followed by evaporation of the solvent to afford 6-aminoquinoxaline as a yellow solid (342 mg, 82% yield) with a thin layer chromatography (TLC) Rf value of 0.32 (unfolding agent: ethyl acetate). The product was characterized by 1H NMR (CDCl3): δ 8.65 (1H, d, J=1.7 Hz), 8.55 (1H, d, J=1.7 Hz), 7.87 (1H, d, J=8.9 Hz), 7.18 (1H, dd, J=8.9,2.5 Hz), 7.13 (1H, d, J=2.5 Hz), 4.20 (2H, br. s, -NH2).

References

[1] Patent: US2012/178748, 2012, A1. Location in patent: Page/Page column 43
[2] Patent: WO2013/6792, 2013, A1. Location in patent: Paragraph 0170
[3] Patent: WO2005/42513, 2005, A1. Location in patent: Page/Page column 71
[4] Heterocycles, 2007, vol. 72, p. 353 - 361
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6169 - 6186

6-Aminoquinoxaline(6298-37-9)Related Product Information

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• 5-Bromo-6-aminoquinoxaline
• Brimonidine Impurity E
• 4,5-Didehydro BriMonidine
• N-(4,5-Dihydro-1H-iMidazol-2-yl)-6-quinoxalinaMine
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• Brimonidine Tartrate Impurity 4
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• 5-BROMO-6-ISOTHIOCYANATE QUINOXALINE
• 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine
• Brimonidine Impurity 14