Zinquin ethyl ester

Base Information

• Chemical Name: Zinquin ethyl ester
• CAS No.: 181530-09-6
• Molecular Formula: C21H22N2O5S
• Molecular Weight: 414.482
• UNII: A806Y8IDMB
• DSSTox Substance ID: DTXSID60171164
• Nikkaji Number: J948.841C
• Wikidata: Q27273743
• ChEMBL ID: CHEMBL2335743

Synonyms:Zinquin ethyl ester;181530-09-6;Zinquin ethyl ester [MI];Ethyl 2-[2-methyl-8-[(4-methylphenyl)sulfonylamino]quinolin-6-yl]oxyacetate;UNII-A806Y8IDMB;A806Y8IDMB;CHEMBL2335743;Acetic acid, 2-((2-methyl-8-(((4-methylphenyl)sulfonyl)amino)-6-quinolinyl)oxy)-, ethyl ester;Zinquinethylester;Zinquin-E;Zinquin(freeacid);Zinquin ethyl ester, ultra pure;SCHEMBL18132175;DTXSID60171164;BGA60629;BDBM50429090;MFCD00797629;AKOS027250764;SB73119;2-Methyl-8-[(4-methylphenyl)sulfonylamino]-6-(ethyloxycarbonylmethyloxy)quinoline;HY-124171;CS-0084629;FT-0675912;Zinquin ethyl ester, >=95% (HPLC), solid;J-008824;Q27273743;ethyl-[2-methyl-8-p-toluenesulfonamido-6-quinolyloxy]acetate;2-[[2-Methyl-8-[[(4-methylphenyl)sulfonyl]amino]-6-quinolinyl]oxy]-acetic acid ethyl ester;2-Methyl-8-(4-methylphenylsulfonylamino)quinolinyl)oxyacetic acid ethyl ester

Chemical Property of Zinquin ethyl ester

Chemical Property:

• Melting Point: 112-114°C
• Boiling Point: 578.0±60.0 °C(Predicted)
• PKA: pK1 (quinoline nitrogen): <2; pK (sulfonamide proton): 9.32
• PSA: 102.97000
• Density: 1.313±0.06 g/cm3(Predicted)
• LogP: 4.74810
• Solubility.: Soluble in ethanol, methanol, dimethyl sulfoxide; slightly solub
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 414.12494298
• Heavy Atom Count: 29
• Complexity: 642

Purity/Quality:

98%min ^*data from raw suppliers

ZinquinEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)COC1=CC(=C2C(=C1)C=CC(=N2)C)NS(=O)(=O)C3=CC=C(C=C3)C
• 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 zinc ion with two nitrogen atoms in the structure. Used for studying the role of zinc in apoptosis. Fluorescence: max. Abs. l = 368nm, max. Em. l = 490nm Determn of intracellular Zn2+ and labile Zn2+ ions. 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 zinc ion with two nitrogen atoms in the structure. Used for studying the role of zinc in apoptosis.Fluorescence: max. Abs. l = 368nm, max. Em. l = 490nm

Technology Process of Zinquin ethyl ester

There total 13 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: 85.0%

p-toluenesulfonyl chloride (98-59-9) + ethyl [(2-methyl-8-aminoquinolin-6-yloxy)acetate] (257892-18-5) → ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate] (181530-09-6)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/ja992709f

Reference yield: 76.0%

6-(2-ethoxy-2-oxoethoxy)-2-methyl-8-(4-methylphenylsulfonamido)quinoline N-oxide (1620101-26-9) → ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate] (181530-09-6)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/ja5053768

Reference yield:

4-hydroxy-2-nitroaniline (610-81-1) → ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate] (181530-09-6)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ja992709f

upstream raw materials:

ethyl bromoacetate

2-methyl-6-hydroxy-8-(p-toluenesulfonamido)quinoline

p-toluenesulfonyl chloride

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

Downstream raw materials:

2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid

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