5-Aminoquinolin-6-ol

Base Information

• Chemical Name: 5-Aminoquinolin-6-ol
• CAS No.: 99512-73-9
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.175
• DSSTox Substance ID: DTXSID401315145
• Nikkaji Number: J35.711A
• Mol file: 99512-73-9.mol

Synonyms:5-aminoquinolin-6-ol;99512-73-9;MFCD11036384;5-Amino-6-quinolinol;5-Amino-6-oxy-chinolin;SCHEMBL7846678;DTXSID401315145;AMY26249;AKOS009996370;AS-43998;CS-0102436;EN300-1295185;A928152

Chemical Property of 5-Aminoquinolin-6-ol

Chemical Property:

• Melting Point: 165-168 °C
• Boiling Point: 354.3±32.0 °C(Predicted)
• PKA: 8.67±0.40(Predicted)
• Density: 1.363±0.06 g/cm3(Predicted)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

5-AMINO-6-HYDROXYQUINOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=C2N)O)N=C1

Technology Process of 5-Aminoquinolin-6-ol

There total 1 articles about 5-Aminoquinolin-6-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

6-hydroxyquinoline (580-16-5) + 1-Methyl-1-phenylhydrazine (618-40-6) → 5-amino-6-hydroxylquinoline (99512-73-9) + N-methylaniline (100-61-8)

Guidance literature:

In ethylene glycol; at 80 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b00421

Reference yield: 50.0%

5-amino-6-hydroxylquinoline (99512-73-9) + 8-fluoro-3-phenylbenzo[e][1,2,4]-triazine → 8-(5-amino-6-quinolinoxy)-3-phenylbenzo[e][1,2,4]triazine

Guidance literature:

5-amino-6-hydroxylquinoline; With sodium hydride; In dimethyl sulfoxide; mineral oil; at 80 ℃; for 0.25h;

8-fluoro-3-phenylbenzo[e][1,2,4]-triazine; In dimethyl sulfoxide; mineral oil; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01074

Reference yield:

5-amino-6-hydroxylquinoline (99512-73-9) → 2-phenyl-3H-quino[6,5-b][1,2,4]triazino[1,6,5-de][1,4]benzoxazin-3-yl

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.25 h / 80 °C

1.2: 1 h / 80 °C / Inert atmosphere

2.1: dichloromethane / 12 h / 30 - 35 °C / Inert atmosphere; Irradiation

With sodium hydride; In dichloromethane; dimethyl sulfoxide; mineral oil;

DOI:10.1021/acs.orglett.0c01074

upstream raw materials:

6-hydroxyquinoline

1-Methyl-1-phenylhydrazine

Downstream raw materials:

quinoline-5,6-dione

Refernces