Quinoline-7,8-oxide

Base Information

• Chemical Name: Quinoline-7,8-oxide
• CAS No.: 130536-39-9
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.161
• DSSTox Substance ID: DTXSID30926789
• Mol file: 130536-39-9.mol

Synonyms:130536-39-9;1a,7b-dihydrooxireno[2,3-h]quinoline;QUINOLINE7,8-OXIDE;Quinoline-7,8-oxide;110288-09-0;Oxireno[h]quinoline,1a,7b-dihydro-(9CI);CCRIS 4437;BRN 4177592;1a,7b-Dihydrooxireno(h)quinoline (+-)-;Oxireno(h)quinoline, 1a,7b-dihydro-, (+-)-;(+-)-7,8-Epoxy-7,8-dihydroquinoline;1a,7b-Dihydrooxireno[h]quinoline;DTXSID30926789;AKOS006279048;(+/-)-7,8-EPOXY-7,8-DIHYDROQUINOLINE

Chemical Property of Quinoline-7,8-oxide

Chemical Property:

• Vapor Pressure: 0.00211mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 299.5°C at 760 mmHg
• Flash Point: 109.9°C
• PSA: 25.42000
• Density: 1.289g/cm³
• LogP: 1.54830
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

QUINOLINE7,8-OXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C3C(O3)C=C2)N=C1

Technology Process of Quinoline-7,8-oxide

There total 12 articles about Quinoline-7,8-oxide 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: 90.0%

5,7-Dibromo-5,6,7,8-tetrahydroquinolin-8-yl acetate (110288-07-8,110288-08-9,130536-44-6) → 7,8-Epoxy-7,8-dihydroquinoline (110288-09-0,130536-39-9,158060-63-0)

Guidance literature:

With sodium methylate; In tetrahydrofuran; 1.) 0 deg C, 2.) room temperature;

Reference yield:

5,6-dihydroquinoline (24334-23-4) → 7,8-Epoxy-7,8-dihydroquinoline (110288-09-0,130536-39-9,158060-63-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / NBA / 2 h / Ambient temperature

2: 86 percent / NBS / CCl₄

3: 72 percent / NaOCH₃ / tetrahydrofuran / 15 h / Ambient temperature

With N-Bromosuccinimide; sodium methylate; N-bromoacetamide; In tetrahydrofuran; tetrachloromethane;

DOI:10.1016/S0040-4039(00)94245-X

Reference yield:

trans-7-Bromo-5,6,7,8-tetrahydroquinolin-8-yl acetate (110288-06-7,130536-42-4) → 7,8-Epoxy-7,8-dihydroquinoline (110288-09-0,130536-39-9,158060-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NBS / CCl₄

2: 72 percent / NaOCH₃ / tetrahydrofuran / 15 h / Ambient temperature

With N-Bromosuccinimide; sodium methylate; In tetrahydrofuran; tetrachloromethane;

DOI:10.1016/S0040-4039(00)94245-X

upstream raw materials:

7,8-Epoxy-5,6,7,8-tetrahydroquinoline

5,7-Dibromo-5,6,7,8-tetrahydroquinolin-8-yl acetate

5,6-dihydroquinoline

trans-7-Bromo-5,6,7,8-tetrahydroquinolin-8-yl acetate

Downstream raw materials:

trans-5,6,7,8-diepoxy-5,6,7,8-tetrahydroquinoline

cis-5,6,7,8-diepoxy-5,6,7,8-tetrahydroquinoline

Refernces

• 1、 Agarwal, Shiv K.,Boyd, Derek R.,Davies, R. Jeremy H.,Hamilton, Lynne,Jerina, Donald M.,et al.. "Synthesis of Arene Oxide and trans-Dihydrodiol Metabolites of Quinoline". . p. 1969 - 1974. Retrieved 2007/10/02.