ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Quinoline compounds 6-Aminoquinoxaline

6-Aminoquinoxaline

Product Name6-Aminoquinoxaline
CAS6298-37-9
MFC8H7N3
MW145.16
EINECS662-890-2
MOL File6298-37-9.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2

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

6639-87-8

6298-37-9

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

Chemical Properties

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Usage And Synthesis

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