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Sigma-Aldrich

2-Quinolinecarboxaldehyde

97%

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Synonym(s):
2-Formylquinoline, 2-Quinolinecarbaldehyde, 2-Quinolylaldehyde, 2-Quinolylcarbaldehyde
Empirical Formula (Hill Notation):
C10H7NO
CAS Number:
Molecular Weight:
157.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

70-72 °C (lit.)

SMILES string

[H]C(=O)c1ccc2ccccc2n1

InChI

1S/C10H7NO/c12-7-9-6-5-8-3-1-2-4-10(8)11-9/h1-7H

InChI key

WPYJKGWLDJECQD-UHFFFAOYSA-N

Application

2-Quinolinecarboxaldehyde was used in the preparation of:
  • 3-(2-quinolyl)-1-phenyl-2-propenone via rapid, tandem aldol-Michael reactions with the lithium, sodium and potassium enolates of acetophenone
  • imine-type ligands
  • sugar-quinoline fluorescent sensor for the detection of Hg2+ in natural water

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Shengju Ou et al.
Chemical communications (Cambridge, England), (42)(42), 4392-4394 (2006-10-24)
A selective and sensitive fluorescent sensor for detection of Hg2+ in natural water was achieved by incorporating the well-known fluorophore quinoline group and a water-soluble D-glucosamine group within one molecule.
Addressing the unusual reactivity of 2-pyridinecarboxaldehyde and 2-quinolinecarboxaldehyde in base-catalyzed aldol reactions with acetophenone.
Wachter-Jurcsak N, et al.
Tetrahedron Letters, 39(23), 3903-3906 (1998)
Copper (I)-imine complexes: Synthesis and catalytic activity in olefin cyclopropanation
Attilio Ardizzoia G, et al.
Inorgorganica Chimica Acta, 362(10), 3507-3512 (2009)
Diana Costa et al.
Biomacromolecules, 18(9), 2928-2936 (2017-08-17)
The development of a suitable delivery system and the targeting of intracellular organelles are both essential for the success of drug and gene therapies. The conception of fluorescent ligands, displaying targeting specificity together with low toxicity, is an emerging and
Sakthi Raje et al.
Chemistry, an Asian journal, 13(11), 1458-1466 (2018-04-01)
Koneramines (LR OR', R=Ph or Ts; R'=Me, iPr) and their complexes were found to emerge from the system of pyridine-2-carboxaldehyde and N-phenyl/tosylethylenediamine when a primary or secondary alcohol was used as solvent. Imidazolidinylpyridines (LR , R=Ph or Ts) became major

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