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Quinoline-5-carboxaldehyde

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Quinoline-5-carboxaldehyde Basic information
Product Name:Quinoline-5-carboxaldehyde
Synonyms:Quinoline-5-carbaldehyde(QUC);quinoline-5-carbaldehyde(SALTDATA: FREE);5-Formylquinoline;Quinoline-5-carboxaldehyde, 97+%;CHEMBRDG-BB 4300479;5-Formylquinoline, 5-Formyl-1-azanaphthalene;5-Quinolinecarbaldehyde;RARECHEM AK ML 0025
CAS:22934-41-4
MF:C10H7NO
MW:157.17
EINECS:681-853-1
Product Categories:ALDEHYDE;Quinoline Derivertives
Mol File:22934-41-4.mol
Quinoline-5-carboxaldehyde Structure
Quinoline-5-carboxaldehyde Chemical Properties
Melting point 95-96°C
Boiling point 314.3±15.0 °C(Predicted)
density 1.223±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
form solid
pka3.94±0.12(Predicted)
AppearanceYellow to brown Solid
Water Solubility Slightly soluble in water.
Sensitive Air Sensitive
BRN 113095
InChI1S/C10H7NO/c12-7-8-3-1-5-10-9(8)4-2-6-11-10/h1-7H
InChIKeyBNEVFKZLYCGDFG-UHFFFAOYSA-N
SMILESO=Cc1cccc2ncccc12
CAS DataBase Reference22934-41-4(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38-43
Safety Statements 26-36/37/39-36/37
WGK Germany WGK 3
HazardClass IRRITANT
HS Code 2933499090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
MSDS Information
ProviderLanguage
ALFA English
Quinoline-5-carboxaldehyde Usage And Synthesis
UsesQuinoline-5-carboxaldehyde is used as a precursor in the preparation of pharmaceuticals.
Synthesis
5-Bromoquinoline

4964-71-0

N,N-Dimethylformamide

68-12-2

Quinoline-5-carboxaldehyde

22934-41-4

General method: n-Butyllithium (2.5 M hexane solution, 300 μL, 0.72 mmol) was added slowly and dropwise to a solution of anhydrous THF (1.5 mL) of 5-bromoquinoline (100 mg, 0.48 mmol) at -78°C. The reaction solution turned red immediately. The reaction solution immediately turned red, followed by the addition of N,N-dimethylformamide (192 μL, 2.49 mmol). After maintaining the reaction temperature at -78 °C with stirring for 10 min, the reaction was quenched with deionized water (6 mL). The reaction mixture was poured into saturated aqueous sodium bicarbonate solution (10 mL) and extracted with ethyl acetate (3 × 10 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: n-hexane solution of 10% ethyl acetate) to give 5-quinolinecarboxaldehyde as a yellow solid in 53% yield.

References[1] European Journal of Medicinal Chemistry, 2019, p. 290 - 320
Quinoline-5-carboxaldehyde Preparation Products And Raw materials
Raw materials5-Bromoquinoline-->N,N-Dimethylformamide-->n-Butyllithium-->Tetrahydrofuran-->Hexane
Preparation Productsα-Methyl-6-quinolinemethanol-->2-(quinolin-5-yl)ethanamine
Tag:Quinoline-5-carboxaldehyde(22934-41-4) Related Product Information
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