6-Aminoquinoxaline

Bezeichnung:6-Aminoquinoxaline

CAS-Nr6298-37-9

Englisch Name:6-Aminoquinoxaline

CBNumberCB3712935

SummenformelC8H7N3

Molgewicht145.16

MOL-Datei6298-37-9.mol

6-Aminoquinoxaline physikalisch-chemischer Eigenschaften

Schmelzpunkt	159 °C
Siedepunkt	254.27°C (rough estimate)
Dichte	1.2109 (rough estimate)
Brechungsindex	1.5400 (estimate)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	2.57±0.30(Predicted)
Farbe	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 Datenbank	6298-37-9(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-36/38-22
S-Sätze:	24/25-36/39-26
WGK Germany	1
HazardClass	IRRITANT
HS Code	29339900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2

Gefahreninformationscode (GHS)

6-Aminoquinoxaline Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
Yellow solid
Verwenden
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.
Synthese

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).
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

6-Aminoquinoxaline Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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