73776-20-2

Basic information

• Product Name: 7-Quinolinecarboxylicacid,8-hydroxy-,methylester(6CI,9CI)
• Synonyms: 7-Quinolinecarboxylicacid,8-hydroxy-,methylester(6CI,9CI);Methyl 8-hydroxyquinoline-7-carboxylate
• CAS NO: 73776-20-2
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.196
• Product Categories: QUINOLINE
• Mol File: 73776-20-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-Quinolinecarboxylicacid,8-hydroxy-,methylester(6CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Quinolinecarboxylicacid,8-hydroxy-,methylester(6CI,9CI)(73776-20-2)
• EPA Substance Registry System: 7-Quinolinecarboxylicacid,8-hydroxy-,methylester(6CI,9CI)(73776-20-2)

Safety Data

• Hazardous Substances Data: 73776-20-2(Hazardous Substances Data)

Usage

General Description

7-Quinolinecarboxylic acid, 8-hydroxy-, methyl ester (6CI, 9CI) is a chemical compound with the molecular formula C10H9NO3. It is a methyl ester derivative of 8-hydroxyquinolinecarboxylic acid, and it is commonly used as a building block in organic synthesis. 7-Quinolinecarboxylicacid,8-hydroxy-,methylester(6CI,9CI) is a yellow powder with a molecular weight of 191.18 g/mol. It is soluble in organic solvents such as ethanol and acetone, but it is sparingly soluble in water. Its primary use is as a starting material in the production of pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, it has potential applications as a chelating agent and as a precursor to various pharmaceuticals and dyes.

Upstream product

• 3724-55-8 methyl but-3-enoate 
• 53636-56-9 methyl 3-bromopicolinate 
• 67-56-1 methanol 
• 19829-79-9 8-hydroxy-7-quinolinecarboxylic acid 

Downstream Products

• 1101929-86-5 C₁₈H₁₅NO₃ 
• 1101929-88-7 C₆₀H₄₈N₆O₁₂ 
• 1101929-87-6 C₁₇H₁₂FNO₂ 
• 630414-70-9 8-benzyloxyquinoline-7-carboxylic acid 
• 1374193-98-2 4-amino-6-((1-(8-(3,5-difluorophenyl)-7-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1374193-76-6 N-(1-(8-(3,5-difluorophenyl)quinolin-7-yl)ethyl)-2-methylpropane-2-sulfinamide 
• 1374193-62-0 (E)-N-((8-(3,5-difluorophenyl)quinolin-7-yl)methylene)-2-methylpropane-2-sulfinamide 
• 1374193-48-2 8-(3,5-difluorophenyl)quinoline-7-carbaldehyde 
• 1374193-41-5 (8-(3,5-difluorophenyl)quinolin-7-yl)methanol 
• 1374193-31-3 methyl 8-(3,5-difluorophenyl)quinoline-7-carboxylate 
• 1312682-38-4 N-(1-(8-(3,5-difluorophenyl)quinolin-7-yl)ethyl)-9H-purin-6-amine 
• 1312684-75-5 1-[8-(3,5-difluorophenyl)quinolin-7-yl]ethanamine 
• 1352717-26-0 5-[(6-chloropyridin-3-yl)methyl]-8-[(1S,2S)-2-hydroxycyclohexyl]-1,8-phenanthrolin-7(8H)-one 
• 1352717-49-7 5-bromo-8-((1S,2S)-2-hydroxycyclohexyl)-1,8-phenanthrolin-7(8H)-one 

Relevant articles and documents

Efficient Access to Methyl-1-hydroxy-2-naphthoates and Heterocyclic Analogues

We report the synthesis of methyl-1-hydroxy-2-naphthoate derivatives and heterocyclic analogues using a two-step approach. This short route employs a Heck coupling of a 2-halo-benzoate with methyl 3-butenoate followed by a Dieckmann cyclization, yielding the 1-hydroxynaphthalene-2-carboxylic acid derivatives in the multigram scale.

Oxinobactin and sulfoxinobactin, abiotic siderophore analogues to enterobactin involving 8-hydroxyquinoline subunits: Thermodynamic and structural studies

The synthesis of two new iron chelators built on the tris-l-serine trilactone scaffold of enterobactin and bearing a 8-hydroxyquinoline (oxinobactin) or 8-hydroxyquinoline-5-sulfonate (sulfoxinobactin) unit has been described. The X-ray structure of the ferric oxinobactin has been determined, exhibiting a slightly distorted octahedral environment for Fe(III) and a Δ configuration. The Fe(III) chelating properties have been examined by potentiometric and spectrophotometric titrations in methanol-water 80/20% w/w solvent for oxinobactin and in water for sulfoxinobactin. They reveal the extraordinarily complexing ability (pFeIII values) of oxinobactin over the p[H] range 2-9, the pFe value at p[H] 7.4 being 32.8. This was supported by spectrophotometric competition showing that oxinobactin removes Fe(III) from ferric enterobactin at p[H] 7.4. In contrast, the Fe(III) affinity of sulfoxinobactin was largely lower as compared to oxinobactin but similar to that of the ligand O-TRENSOX having a TREN backbone. These results are discussed in relation to the predisposition by the trilactone scaffold of the chelating units. Some comparisons are also made with other quinoline-based ligands and hydroxypyridinonate ligand (hopobactin).

Oxinobactin, a siderophore analogue to enterobactin involving 8-hydroxyquinoline subunits: Synthesis and iron binding ability

Oxinobactin, a siderophore analogue to enterobactin but possessing 8-hydroxyquinoline instead of catechol complexing subunits, has been synthesized starting from l-serine and 8-hydroxyquinoline. Comparative iron binding studies showed that oxinobactin is as effective as enterobactin for the complexation of FeIII at physiological pH but with improved complexing ability at acidic pH.