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6-Aminoquinoxaline

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CAS:6298-37-9
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  • 2021-10-14
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6-Aminoquinoxaline Basic information
Product Name:6-Aminoquinoxaline
Synonyms:6-QUINOXALINYLAMINE;6-QUINOXALINAMINE;6-AMINOQUINOXALINE;6-Aminoquinoxaline ,99%;QUINOXALIN-6-YLAMINE;6-Aminoquinoxaline/6-quinoxalinamine (for Brimonidine);Quinoxaline-6-amine;6-Quinoxalineamine
CAS:6298-37-9
MF:C8H7N3
MW:145.16
EINECS:662-890-2
Product Categories:Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Quinoxalines;Quinolines, Quinazolines and derivatives;pharmacetical;Amines;Quinolines, Isoquinolines & Quinoxalines;Quinolines, Isoquinolines & Quinoxalines
Mol File:6298-37-9.mol
6-Aminoquinoxaline Structure
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
pka2.57±0.30(Predicted)
color Yellow to Dark Yellow
InChIInChI=1S/C8H7N3/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-5H,9H2
InChIKeyMSGRFBKVMUKEGZ-UHFFFAOYSA-N
SMILESN1C2C(=CC(N)=CC=2)N=CC=1
CAS DataBase Reference6298-37-9(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 Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
MSDS Information
6-Aminoquinoxaline Usage And Synthesis
Chemical PropertiesYellow solid
Uses6-Quinoxalinamine is used in the synthetic preparation and evaluation of novel nitroheterocyclic hypoxic markers for solid tumor.
DefinitionChEBI: 6-Quinoxalinamine is a quinoxaline derivative.
Synthesis
6-NITROQUINOXALINE

6639-87-8

6-Aminoquinoxaline

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 Preparation Products And Raw materials
Raw materialsEthanol-->Palladium-->4-Nitro-o-phenylenediamine-->GLYOXAL SODIUM BISULFITE-->6-NITROQUINOXALINE-->Hydrogen-->Methanol
Tag:6-Aminoquinoxaline(6298-37-9) Related Product Information
Sulfamic acid EC 2.6.1.2 Acetaminophen Quinoxaline Glucosamine Aminopyrine 5-Bromo-6-aminoquinoxaline Brimonidine Impurity E 4,5-Didehydro BriMonidine N-(4,5-Dihydro-1H-iMidazol-2-yl)-6-quinoxalinaMine Hydroxy Brimonidine 5-Bromoquinazolin-6-ylthiourea Brimonidine Tartrate Impurity 4 BriMonidine-2,3-dione Thiourea, N-(2-aminoethyl)-N'-(5-bromo-6-quinoxalinyl)- 5-BROMO-6-ISOTHIOCYANATE QUINOXALINE 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine Brimonidine Impurity 14

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