4363-93-3

Basic information

• Product Name: 4-Quinolinecarboxaldehyde
• Synonyms: AKOS BBS-00005334;4-FORMYLQUINOLINE;4-QUINOLINECARBALDEHYDE;4-QUINOLINECARBOXALDEHYDE;ASINEX-REAG BAS 01118292;CINCHONINALDEHYDE;QUINOLINE-4-ALDEHYDE;QUINOLINE-4-CARBALDEHYDE
• CAS NO: 4363-93-3
• Molecular Formula: C₁₀H₇NO
• Molecular Weight: 157.17
• EINECS: 224-453-0
• Product Categories: Quinoline Derivertives;Quinolinecarboxylic Acids, etc.;Quinolines;Quinoline
• Mol File: 4363-93-3.mol
• Article Data: 38

Chemical Properties

• Melting Point: 45-52 °C(lit.)
• Boiling Point: 131-133°C 5mm
• Flash Point: >230 °F
• Appearance: Off-white to yellow-brown/Crystalline Powder, Chunks, or Solid
• Density: 1.1599 (rough estimate)
• Vapor Pressure: 0.00047mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 2-8°C
• PKA: 2.95±0.13(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• BRN: 113072
• CAS DataBase Reference: 4-Quinolinecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Quinolinecarboxaldehyde(4363-93-3)
• EPA Substance Registry System: 4-Quinolinecarboxaldehyde(4363-93-3)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-36/37/38
• Safety Statements: 24/25-36-26-36/37/39
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 4363-93-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow to yellow-brown crystalline powder

Uses

4-Quinolinecarboxaldehyde was used in the synthesis of lepidylamines. It also shows antimicrobial activity toward human intestinal bacteria such as Clostridium perfringens.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 841, 1970 DOI: 10.1021/jo00828a074

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

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 91-22-5 quinoline 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 6281-32-9 4-quinolylmethanol 
• 611-35-8 4-chloroquinoline 
• 20461-86-3 2,2-diethoxy acetic acid 
• 79-43-6 dichloro-acetic acid 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 87-51-4 indole-3-acetic acid 
• 7446-08-4 selenium(IV) oxide 
• 108-88-3 toluene 
• 123-91-1 1,4-dioxane 
• 7732-18-5 water 
• 5450-80-6 1-[4]quinolylmethyl-pyridinium; iodide 

Downstream Products

• 486-74-8 4-quinolinic acid 
• 55908-34-4 1-Quinolin-4-yl-ethanol 
• 109805-22-3 3c-[4]quinolyl-2-(3,4-dimethoxy-phenyl)-acrylonitrile 
• 141265-66-9 4-[4]quinolylmethylenamino-phenol 
• 53274-27-4 diethyl 1,4-dihydro-2,6-dimethyl-4-(4-quinolinyl)pyridine-3,5-dicarboxylate 
• 109558-06-7 benzoyloxy-[4]quinolyl-acetonitrile 
• 680590-98-1 ethyl-[4]quinolylmethyl-amine 
• 1477-60-7 4-quinolinecarboxaldehyde thiosemicarbazone 

Relevant articles and documents

Synthesis of cinchoninic acid, quininic acid and of the corresponding aldehydes

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Synthetic approaches to Cinchona alkaloids: The C-8/C-9 disconnection strategy

When conducted in DMSO, the Hünig's base-promoted condensation of 3-quinuclidinone with quinoline-4-carboxaldehyde gave an equimolar mixture of epimeric aldols 8 with an excellent yield.

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity

Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.