ZINQUIN ETHYL ESTER

Base Information

• Chemical Name: ZINQUIN ETHYL ESTER
• CAS No.: 151606-29-0
• Molecular Formula: C19H18 N2 O5 S
• Molecular Weight: 414.47
• Mol file: 151606-29-0.mol

Synonyms:Aceticacid, [[2-methyl-8-[[(4-methylphenyl)sulfonyl]amino]-6-quinolinyl]oxy]- (9CI);Zinquin; Zinquin A

Chemical Property of ZINQUIN ETHYL ESTER

Chemical Property:

• Vapor Pressure: 1.23E-15mmHg at 25°C
• Melting Point: 112-114°C
• Boiling Point: 608°C at 760 mmHg
• PKA: pK1 (quinoline nitrogen): <2; pK (carboxylic acid proton): 5
• Flash Point: 321.5°C
• PSA: 102.97000
• Density: 1.412g/cm³
• LogP: 4.74810
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble

Purity/Quality:

98%,99%, ^*data from raw suppliers

Zinquin ethyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: A fluorescent reagent and indicator of intracellular zinc ions. An analogue of widely used indicator, TS-Q. Zinquin ethyl ester is membrane permeable therefore useful to detect intracellular zinc ions. Zinquin ethyl ester forms a complex with a zin Zinquin ethyl ester is a lipophilic, zinc-sensitive, cell-permeable fluorescnet probe.

Technology Process of ZINQUIN ETHYL ESTER

There total 10 articles about ZINQUIN ETHYL ESTER 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: 72.0%

ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate] (181530-09-6) → 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid (151606-29-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; for 4h; Heating;

DOI:10.1021/ja992709f

Reference yield:

4-hydroxy-2-nitroaniline (610-81-1) → 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid (151606-29-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 52 percent / aq. HCl; phosphoric acid / 3 h / 95 °C

2: 54 percent / diisopropylethylamine / ethanol / 24 h / Heating

3: 86 percent / H₂ / 5 percent Pd/C / ethanol / 24 h / 20 °C

4: 85 percent / pyridine / 20 °C

5: 72 percent / aq. LiOH / tetrahydrofuran; methanol / 4 h / Heating

With pyridine; hydrogenchloride; lithium hydroxide; phosphoric acid; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 1: Cycloaddition / 2: Condensation / 3: Reduction / 4: Tosylation / 5: Hydrolysis;

DOI:10.1021/ja992709f

Reference yield:

2-methyl-6-hydroxy-8-nitroquinoline (257892-16-3) → 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid (151606-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 54 percent / diisopropylethylamine / ethanol / 24 h / Heating

2: 86 percent / H₂ / 5 percent Pd/C / ethanol / 24 h / 20 °C

3: 85 percent / pyridine / 20 °C

4: 72 percent / aq. LiOH / tetrahydrofuran; methanol / 4 h / Heating

With pyridine; lithium hydroxide; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 1: Condensation / 2: Reduction / 3: Tosylation / 4: Hydrolysis;

DOI:10.1021/ja992709f

upstream raw materials:

[5-Bromo-2-methyl-8-(toluene-4-sulfonylamino)-quinolin-6-yloxy]-acetic acid ethyl ester

ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate]

4-hydroxy-2-nitroaniline

2-methyl-6-hydroxy-8-nitroquinoline

Refernces

• 1、 Mahadevan, Indumathy B.,Kimber, Marc C.,Lincoln, Stephen F.,Tiekink, Edward R.T.,Ward, A. David,Betts, W. Henry,Forbes, Ian J.,Zalewski, Peter D.. "The synthesis of zinquin ester and zinquin acid, zinc(II)-specific fluorescing agents for use in the study of biological zinc(II)". . p. 561 - 568. Retrieved 2007/10/03.