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

• 1780-17-2 quinolin-2-ylmethanol 
• 81124-50-7 (E)-3-(2-quinolinyl)-2-propenoic acid 
• 110-89-4 piperidine 
• 76253-74-2 2-(chloromethyl)quinoline N-oxide 
• 4377-41-7 2-Chloromethylquinoline 
• 79-46-9 2-nitropropane 
• 63332-88-7 N-(Chinol-2-ylmethylen)-4-dimethylamino-anilin-N-oxid 
• 2005-43-8 2-bromoquinoline 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 1335204-96-0 quinolin-2-yl(butylamino)methyldiphenylphosphine oxide 
• 91-63-4 2-methylquinoline 
• 123-75-1 pyrrolidine 
• 110-88-3 1,3,5-Trioxan 

Downstream Products

• 1011-47-8 1-quinolin-2-yl-ethanone 
• 14148-37-9 Chinolin-2-aldehyd-2,4-dinitrophenylhydrazon 
• 95705-00-3 2-(1,3-diphenyl-imidazolidin-2-yl)-quinoline 
• 4401-04-1 (E)-1-(4-methoxyphenyl)-3-(quinolin-2-yl)prop-2-en-1-one 
• 3678-74-8 2-(Diphenylmethyl)quinoline 
• 18831-34-0 4,4'-(quinolin-2-yl-methanediyl)-bis-phenol 
• 1780-17-2 quinolin-2-ylmethanol 
• 93-10-7 quinoline-2-carboxylic acid 
• 7463-70-9 2-quinolinecarboxaldehyde hydrazone 
• 3561-22-6 1,2-di(quinolyl-2)-1,2-ethanedione 
• 5749-82-6 2-hydroxy-1,2-di-quinolin-2-yl-ethanone 
• 41785-92-6 2-(2,6-diphenyl-pyran-4-ylidenemethyl)-quinoline 
• 24613-99-8 2-(quinolin-2′-yl)benzo[d]thiazole 
• 51265-25-9 4-phenyl-2,2′-biquinoline 

Relevant articles and documents

STIMULI - OR BIO- RESPONSIVE COPOLYMERS, THE POLYMERSOMES COMPRISING THE SAME AND THEIR USE IN DRUG DELIVERY

The present invention concerns amphiphilic copolymers that may be photo- or redox-cleavable and that may assemble into polymersomes. It also concerns their process of preparation and their use as drug carriers.

Iodine-Catalyzed Construction of Dihydrooxepines via 3-Methyl-5-Pyrazolones C?H Oxidation/Functionalization of Quinolines Cascade

An efficient iodine-catalyzed [3+3+1] annulation for the construction of dihydrooxepine scaffolds with quinoline units was developed. This strategy involves a seven-membered dihydrooxepine with a broad substrate scope through a formal three-component tandem reaction. Further derivation of the target product produced a trioxabicycle scaffold, which formed the basic core of natural products and pharmaceutical molecules.

Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer

Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.