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Chemical Structure| 14510-06-6 Chemical Structure| 14510-06-6
Chemical Structure| 14510-06-6

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8-Hydroxyquinoline-2-carbaldehyde is a quinoline derivative containing both hydroxyl and aldehyde groups, with antibacterial, antioxidant, and metal chelation activities. It is widely used in fluorescent probes, biomarker research, and coordination chemistry, with potential value in developing new antimicrobial and anticancer drugs.

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Product Details of 8-Hydroxyquinoline-2-carbaldehyde

CAS No. :14510-06-6
Formula : C10H7NO2
M.W : 173.17
SMILES Code : OC1=C2N=C(C=O)C=CC2=CC=C1
MDL No. :MFCD00168962
InChI Key :SLBPIHCMXPQAIQ-UHFFFAOYSA-N
Pubchem ID :599342

Safety of 8-Hydroxyquinoline-2-carbaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 8-Hydroxyquinoline-2-carbaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14510-06-6 ]

[ 14510-06-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 14510-06-6 ]
  • [ 21080-80-8 ]
  • [ 934-22-5 ]
  • [ 1024610-97-6 ]
YieldReaction ConditionsOperation in experiment
41% Compound 446: 1 -(1 H-Benzoimidazol-S-ylJ^-cyclopropanecarbonyl-S-hydroxy-S-tdelta- hydroxy-quinolin-2-yl)-1 ,5-dihydro-pyrrol-2-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) and 8-Hydroxy-quinoline-2-carbaldehyde (1 mmol) were added to ethanol (5 ml). After 30 min 3 4-Cyclopropyl-2,4-dioxo-butyric acid ethyl ester (1 EPO <DP n="188"/>mmol) was added. The reaction was heated to 500C and stirred for 24h. After evaporation of the solvent the residue was purified with chromatographic methods.molecular weight (g/mol): 426.44 IC50 hQC (nM): 1.35Yield: 0.174g (41 percent); mp: 155°C, 1H NMR delta 0.67-0.71 (m, 1 H, CH2), 0.77-0.85 (m, 2 H, CH2), 0.88-0.93 (m, 1 H, CH2), 2.85-2.96 (CH-CH2), 6.39 (s, 1 H, CH-N), 6.99 (dd, 3J=6.4 Hz, 4J=1.2 Hz, 1 H, Ar), 7.22 (dd, 3J=7.0 Hz, 4J=1.2 Hz, 1 H, Ar), 7.31 (t, 3J=7.8 Hz, 1 H, Ar), 7.51 (d, 3J=8.6 Hz, 1 H, Ar), 7.60 (d, 3J=9.0 Hz, 1 H, Benzimid), 7.75 (dd, 3J=9.0 Hz, 4J=1.9 Hz, 1 H, Ar), 8.09-8.1 1 (m, 2 H, Benzimid), 9.03 (s, 1 H, Benzimid), 9.53 (s, br., 1 H, NH); MS m/z 427.0 (M+H)+, HPLC (254 nm): rt 2.81 min (100 percent)
  • 2
  • [ 14510-06-6 ]
  • [ 29390-67-8 ]
  • 6A-deoxy-6A-[(8-hydroxyquinolyl)-2-methylamino]-β-cyclodextrin [ No CAS ]
  • 3
  • [ 14510-06-6 ]
  • [ 66640-86-6 ]
  • 8-hydroxyquinolylbiotin hydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In ethanol; for 24h;Reflux; 8-Hydroxy-2-quinolinecarboxaldehyde (47mg, 0.27mmol) was added to <strong>[66640-86-6]biotin hydrazide</strong> (70mg, 0.27mmol) in absolute ethanol (25mL). The reaction was refluxed under stirring for 24h. After cooling, the product precipitated and then was collected by filtration and recrystallized from ethanol. (0047) Yield: 88mg (79percent); Positive ion ESI-MS: m/z=414.1 [P+H]+, 436.1 [P+Na]+, 826.8 [2P+H]+, 848.8 [2P+Na]+; 1H NMR (500MHz, (CD3)2SO) delta (ppm): 11.70 (s, NH, isomer B), 11.64 (s, NH, isomer A), 9.79 (s, OH), 8.36 (s, CH=N, isomer B), 8.31 (d, J4,3=8.7Hz, H-4 of HQ), 8.21 (s, CH=N, isomer A), 8.02 (m, H-3 of HQ), 7.49?7.34 (m, H-5 and H-6 of HQ), 7.11 (t, J=7.0Hz, H-7), 6.42 (s, H-11 of biotin), 6.34 (s, H-13 of biotin), 4.31 (m, H-9 of biotin), 4.15 (m, H-10 of biotin), 3.14 (m, H-6 of biotin), 2.82 (m, H-8 of biotin), 2.72 (t, J=7.4Hz, Hs-2 of biotin, isomer A), 2.58 (m, H-8? of biotin), 2.28 (m, H-2 of biotin, isomer B), 1.67 (m, H-5 and Hs-3 of biotin), 1.59?1.35 (m, Hs-4 and H-5? of biotin). 13C NMR (125MHz, (CD3)2SO) delta (ppm): 175.2 (C=O, isomer A), 169.13 (C=O, isomer B), 163.2 (C-12 of biotin), 154.1 (C-8 of HQ), 152.1 (C-2 of HQ), 146.6 (CH=N, isomer B), 143.2 (CH=N, isomer A), 138.6 (C-9 of HQ), 136.9 (C-4 of HQ), 135.0 (C-10 of HQ), 128.5 (C-6 of HQ), 118.0 (C-3 and C-5 of HQ), 112.5 (C-7 of HQ), 61.4 (C-10 of biotin), 59.6 (C-9 of biotin), 55.8 (C-6 of biotin), 40.2 (C-8 of biotin), 34.4 (C-2 of biotin, isomer B), 32.1 (C-2 of biotin, isomer A), 28.6 (C-4 and C-5 of biotin), 24.9 (C-3 of biotin).
 

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Technical Information

• Appel Reaction • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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