5470-96-2

Basic information

• Product Name: 2-Quinolinecarboxaldehyde
• Synonyms: QUINOLINE-2-CARBALDEHYDE;QUINOLINE-2-CARBOXALDEHYDE;TIMTEC-BB SBB004007;2-FORMYLQUINOLINE;2-QUINOLINECARBALDEHYDE;2-QUINOLINECARBOXALDEHYDE;Quinaldehyde;Quinoline-2-carboxaldehyde,98%
• CAS NO: 5470-96-2
• Molecular Formula: C10H7NO
• Molecular Weight: 157.17
• EINECS: 226-804-3
• Product Categories: Quinoline&Isoquinoline;Quinoline Derivertives;Quinolinecarboxylic Acids, etc.;Quinolines;Quinoline;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 5470-96-2.mol
• Article Data: 82

Chemical Properties

• Melting Point: 70-72 °C(lit.)
• Boiling Point: 314.3 °C at 760 mmHg
• Flash Point: 151.9 °C
• Appearance: Orange to brown/Crystals or Crystalline Powder
• Density: 1.223 g/cm³
• Vapor Pressure: 0.00047mmHg at 25°C
• Refractive Index: 1.687
• Storage Temp.: Refrigerator (+4°C)
• PKA: 3.74±0.40(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 113061
• CAS DataBase Reference: 2-Quinolinecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinolinecarboxaldehyde(5470-96-2)
• EPA Substance Registry System: 2-Quinolinecarboxaldehyde(5470-96-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 5470-96-2(Hazardous Substances Data)

Usage

Description

2-Quinolinecarboxaldehyde is an organic compound that belongs to the quinoline family. It is a white to light yellow crystal powder and is known for its chemical reactivity and diverse applications in various industries.

Uses

Used in Chemical Synthesis:
2-Quinolinecarboxaldehyde is used as a key intermediate in the synthesis of various organic compounds. It is particularly useful in the preparation of 3-(2-quinolyl)-1-phenyl-2-propenone through rapid, tandem aldol-Michael reactions with the lithium, sodium, and potassium enolates of acetophenone. This application is significant in the development of new chemical compounds and materials.
Used in Coordination Chemistry:
In coordination chemistry, 2-Quinolinecarboxaldehyde is used to synthesize imine-type ligands. These ligands are essential in the formation of metal complexes, which have a wide range of applications, including catalysis, sensing, and pharmaceuticals.
Used in Environmental Science:
2-Quinolinecarboxaldehyde is also used in the development of sugar-quinoline fluorescent sensors for the detection of Hg2+ ions in natural water. This application is crucial for environmental monitoring and ensuring the safety of water resources.

Purification Methods

Distil it in steam and recrystallise it from H2O. Protect it from light. The semicarbazone has m 254o (from aqueous EtOH), and the picrate has m 197-199o. [Beilstein 21 H 322, 21 III/IV 4034, 21/8 V 442.]

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

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 91-22-5 quinoline 
• 4377-41-7 2-Chloromethylquinoline 
• 79-46-9 2-nitropropane 
• 67-56-1 methanol 
• 5662-03-3 2-(1H-quinolin-2-ylidene)-indan-1,3-dione 
• 98-95-3 nitrobenzene 
• 91-63-4 2-methylquinoline 
• 100-46-9 benzylamine 
• 93-10-7 quinoline-2-carboxylic acid 
• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 528-75-6 2,4-dinitrobenzaldehyde 
• 1780-17-2 quinolin-2-ylmethanol 
• 63332-88-7 N-(Chinol-2-ylmethylen)-4-dimethylamino-anilin-N-oxid 

Downstream Products

• 119118-42-2 (E)-1-phenyl-3-(quinolin-2-yl)prop-2-en-1-one 
• 97258-49-6 3-[2]quinolyl-1,5-diphenyl-pentane-1,5-dione 
• 883557-48-0 {5-[2-((E)-2-Quinolin-2-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine 
• 223446-84-2 (NC₉H₆CHO)Zn(SC₆F₅)2 
• 1029017-32-0 1-(1-phenylethyl)-3-(2-quinolinylmethylidenyl)indolin-2-one 
• 1029017-25-1 1-benzyl-3-(2-quinolinylmethylidenyl)indolin-2-one 
• 5603-18-9 1-phenyl-N-(quinolin-2-ylmethylene)methanamine 

Relevant articles and documents

Iodine-Promoted Synthesis of Dipyrazolo/Diuracil-Fused Pyridines and o-Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4-Methylazaarenes

The iodine-promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene-substituted bis-pyrazolo[3,4-b:4′,3′-e]pyridines (BPPs), diuracilpyridines and o-amino diheteroaryl ketones. The domino procedure proceeded with easily available methyl azaarenes, 5-aminouracils and substituted 5-aminopyrazoles. This protocol is a simple and metal-free approach which exhibits high functional group compatibility and broad substrates scope. Moreover, this transformation can be applied for the preparation of dipyrazolo/diuracil-fused pyridines on a gram scale. (Figure presented.).

A Metal- and Azide-free Oxidative Coupling Reaction for the Synthesis of [1,2,3]Triazolo[1,5-a]quinolines and their Application to Construct C?C and C-P Bonds, 2-Cyclopropylquinolines and Imidazo[1,5-a]quinolines

An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5-a]quinolines from methyl azaarenes and N-tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram-scale. 1,2,3-Triazoles are an important skeletal structure for the construction of C?C and C?P bonds, 2-cyclopropylquinolines and imidazo[1,5-a]quinolines, for which different synthetic applications were explored. (Figure presented.).

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.