N-(6-Methoxy-8-quinolyl)-4-toluenesulfonamide

Base Information

• Chemical Name: N-(6-Methoxy-8-quinolyl)-4-toluenesulfonamide
• CAS No.: 109628-27-5
• Molecular Formula: C17H16 N2 O3 S
• Molecular Weight: 328.392
• NSC Number: 120213
• UNII: 7SWW052N6R
• DSSTox Substance ID: DTXSID00148996
• Nikkaji Number: J455.308J
• Wikipedia: 6-methoxy-(8-p-toluenesulfonamido)quinoline
• Wikidata: Q7671630
• ChEMBL ID: CHEMBL1445650
• Mol file: 109628-27-5.mol

Synonyms:6-methoxy-8-(4-toluenesulfonamide)quinoline;6-TSQ;N-(6-methoxy-8-quinolyl)-4-toluenesulfonamide;N-(6-methoxy-8-quinolyl)-p-toluenesulfonamide;TS-Q;TSQ-6N

Chemical Property of N-(6-Methoxy-8-quinolyl)-4-toluenesulfonamide

Chemical Property:

• Vapor Pressure: 7.27E-11mmHg at 25°C
• Melting Point: 133–134 ℃
• Boiling Point: 518.8°Cat760mmHg
• Flash Point: 267.5°C
• PSA: 76.67000
• Density: 1.334g/cm³
• LogP: 4.50640
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in ethanol, methanol
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 328.08816355
• Heavy Atom Count: 23
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

TSQ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC2=C3C(=CC(=C2)OC)C=CC=N3
• Uses: Determn of extracellular and intracellular Zn2+ levels in biological systems. Zn+ selective probe in the presence of Mg+ and Ca+.

Technology Process of N-(6-Methoxy-8-quinolyl)-4-toluenesulfonamide

There total 3 articles about N-(6-Methoxy-8-quinolyl)-4-toluenesulfonamide 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: 79.0%

6-methoxyquinolin-8-amine (90-52-8) + p-toluenesulfonyl chloride (98-59-9) → N-(6-methoxy-8-quinolinyl)-4-methylbenzenesulfonamide (109628-27-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.9b00942

Reference yield:

4-methoxy-2-nitroaniline (96-96-8) → N-(6-methoxy-8-quinolinyl)-4-methylbenzenesulfonamide (109628-27-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium iodide / 0.08 h / 20 °C

1.2: 0.17 h / Cooling with ice

1.3: 2 h / 140 °C

2.1: pyrographite; hydrazine hydrate / methanol / 12 h / 80 °C

3.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyrographite; hydrazine hydrate; triethylamine; sodium iodide; In methanol; dichloromethane;

DOI:10.1021/acs.joc.9b00942

Reference yield:

6-methoxy-8-nitroquinoline (85-81-4) → N-(6-methoxy-8-quinolinyl)-4-methylbenzenesulfonamide (109628-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyrographite; hydrazine hydrate / methanol / 12 h / 80 °C

2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyrographite; hydrazine hydrate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/acs.joc.9b00942

upstream raw materials:

6-methoxyquinolin-8-amine

p-toluenesulfonyl chloride

4-methoxy-2-nitroaniline

6-methoxy-8-nitroquinoline

Refernces

• 1、 -. "NEUROPROTECTIVE QUINOLINE SULFONAMIDES". Paragraph 0041. . Retrieved 2020/07/07.