8-Acetoxyquinoline

Base Information

• Chemical Name: 8-Acetoxyquinoline
• CAS No.: 2598-29-0
• Molecular Formula: C11H9NO2
• Molecular Weight: 187.198
• Hs Code.: 2933499090
• European Community (EC) Number: 219-999-1
• NSC Number: 508813
• UNII: 9CKX3NX6YT
• DSSTox Substance ID: DTXSID30180642
• Nikkaji Number: J39.112C
• Wikidata: Q83051219
• Mol file: 2598-29-0.mol

Synonyms:8-Acetoxyquinoline;quinolin-8-yl acetate;2598-29-0;8-Quinolyl acetate;8-Quinolinol, 8-acetate;8-Acetyloxyquinoline;8-Quinolinol acetate;8-Quinolinol, acetate (ester);8-Quinolinol, acetate;CCRIS 7823;EINECS 219-999-1;9CKX3NX6YT;NSC 508813;BRN 0135053;NSC-508813;5-21-03-00258 (Beilstein Handbook Reference);8-Acetoxychinolin;Fennosan-H-30;8-Quinolinol,8-acetate;8-Quinolinyl acetate #;UNII-9CKX3NX6YT;SCHEMBL250301;DTXSID30180642;MFCD00014665;NSC508813;STK386377;AKOS001704197;SB67576;AS-58068;LS-142477;EU-0017835;FT-0600554;A20618;D95898;SR-01000513197;J-016206;SR-01000513197-1

Chemical Property of 8-Acetoxyquinoline

Chemical Property:

• Vapor Pressure: 0.000294mmHg at 25°C
• Melting Point: 56-57°C
• Refractive Index: 1.609
• Boiling Point: 321.642 °C at 760 mmHg
• PKA: 2.83±0.17(Predicted)
• Flash Point: 148.324 °C
• PSA: 39.19000
• Density: 1.212 g/cm³
• LogP: 2.16010
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 187.063328530
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Quinolin-8-ylacetate 97% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=CC2=C1N=CC=C2

Technology Process of 8-Acetoxyquinoline

There total 9 articles about 8-Acetoxyquinoline 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: 98.0%

8-quinolinol (148-24-3,24804-14-6) + acetic anhydride (108-24-7) → 8-acetyloxyquinoline (2598-29-0)

Guidance literature:

With sulfuric acid; for 16h; Ambient temperature;

DOI:10.1021/jo00205a043

Reference yield: 51.4%

8-quinolinol (148-24-3,24804-14-6) + formic acid (64-18-6) + acetic anhydride (108-24-7) → 8-acetyloxyquinoline (2598-29-0)

Guidance literature:

8-quinolinol; formic acid; acetic anhydride; at 60 ℃; for 1h; Inert atmosphere;

With sodium acetate; In toluene; at 0 - 20 ℃; for 2h;

DOI:10.1055/s-0040-1707187

Reference yield: 51.0%

acetic anhydride (108-24-7) + 8-quinolyloxytriphenylbismuth chloride (90179-61-6) + acetic acid (64-19-7,77671-22-8) → 8-acetyloxyquinoline (2598-29-0) + 7-phenyl-8-quinolyl acetate (105071-87-2)

Guidance literature:

Yield given. Multistep reaction; 1.) toluene, reflux, 14 h, 2.) reflux, 3 h;

upstream raw materials:

8-quinolinol

acetic anhydride

acetyl chloride

8-hydroxy-7-phenylquinoline

Downstream raw materials:

3-phenyl-butan-2-one

4-Phenyl-2-butanone

quinolin-8-yl-4-methoxybenzoate

quinolin-8-yl 4-chlorobenzoate

Refernces

• 1、 -. "One-pot method for preparing chloroquine chloroquine and diiodoquinoline". Paragraph 0024-0027; 0034-0037; 0044-0046; 0050-0052; 0056. . Retrieved 2021/08/25.
• 2、 Wang, Yazhen,Yu, Feihu,Han, Xiao,Li, Ming,Tong, Yue,Ding, Jie,Hou, Hongwei. "From Surprising Solvothermal Reaction to Uncommon Zinc(II)-Catalyzed Aromatic C-H Activation Reaction for Direct Nitroquinoline Synthesis". supporting information. p. 5953 - 5958. Retrieved 2017/05/22.