| Identification | More | [Name]
6-Aminoquinoxaline | [CAS]
6298-37-9 | [Synonyms]
6-AMINOQUINOXALINE
6-QUINOXALINAMINE
6-QUINOXALINYLAMINE
QUINOXALIN-6-YLAMINE
6-Aminoquinoxaline/6-quinoxalinamine (for Brimonidine)
6-Aminoquinoxaline ,99%
Quinoxaline-6-amine | [EINECS(EC#)]
662-890-2 | [Molecular Formula]
C8H7N3 | [MDL Number]
MFCD00462821 | [Molecular Weight]
145.16 | [MOL File]
6298-37-9.mol |
| Chemical Properties | Back Directory | [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 | [Detection Methods]
HPLC | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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 |
|
|