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

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CAS No.: 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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