335196-05-9

Basic information

• Product Name: 2-CHLORO-8-ETHYL-QUINOLINE-3-CARBALDEHYDE
• Synonyms: AKOS BB-7550;2-CHLORO-8-ETHYL-QUINOLINE-3-CARBALDEHYDE;2-CHLORO-8-ETHYLQUINOLINE-3-CARBOXALDEHYDE;OTAVA-BB 7020617819
• CAS NO: 335196-05-9
• Molecular Formula: C₁₂H₁₀ClNO
• Molecular Weight: 219.6669
• Mol File: 335196-05-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 360.3°C at 760 mmHg
• Flash Point: 171.7°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 2.24E-05mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 2-CHLORO-8-ETHYL-QUINOLINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-8-ETHYL-QUINOLINE-3-CARBALDEHYDE(335196-05-9)
• EPA Substance Registry System: 2-CHLORO-8-ETHYL-QUINOLINE-3-CARBALDEHYDE(335196-05-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 335196-05-9(Hazardous Substances Data)

Usage

General Description

2-Chloro-8-ethyl-quinoline-3-carbaldehyde is a chemical compound with the molecular formula C13H11ClN2O. It is a yellow solid with a molecular weight of 242.69 g/mol. 2-CHLORO-8-ETHYL-QUINOLINE-3-CARBALDEHYDE is used in the synthesis of pharmaceutical products and agrochemicals due to its ability to form various heterocyclic compounds. It has been studied for its potential antimicrobial, antifungal, and antiviral activities. This chemical has also been researched for its potential use in the treatment of a variety of diseases, including cancer. 2-Chloro-8-ethyl-quinoline-3-carbaldehyde is a versatile compound with potential applications in medicinal chemistry and drug discovery.

InChI:InChI=1/C12H10ClNO/c1-2-8-4-3-5-9-6-10(7-15)12(13)14-11(8)9/h3-7H,2H2,1H3

Upstream product

• 33098-65-6 2-acetamido-1-ethylbenzene 
• 578-54-1 ortho-ethylaniline 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 880105-72-6 2-chloro-3-cyano-8-ethylquinoline 
• 436088-08-3 C₁₂H₁₁NO₂ 
• 1100051-02-2 8-ethyl-2-phenylethynyl-quinoline-3-carbaldehyde 
• 1122022-24-5 C₁₈H₁₄ClFN₂ 
• 1122022-31-4 C₁₉H₁₇ClN₂ 
• 1017429-39-8 C₁₂H₁₂ClNO 
• 1163772-59-5 6-ethyl-1-Methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline 
• 1236228-74-2 8-ethyl-1-phenyl-1H-pyrazolo[3,4-h]quinoline 
• 1263317-01-6 6-ethyl-4-iodo-1-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline 
• 1421925-39-4 8-ethyl-2-(phenylethynyl)quinoline-3-carboxylic acid methyl ester 
• 1421925-54-3 6-ethyl-3-phenyl-1H-pyrano[4,3-b]quinolin-1-one 
• 1446868-46-7 C₂₇H₂₀ClN₅O₅S 
• 1446868-24-1 C₂₃H₁₇Cl₂N₃O₂S 
• 1446868-01-4 C₂₁H₁₆ClN₃OS 

Relevant articles and documents

2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier-Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides

TCTA-DMF (2,4,6-trichloro-1,3,5-triazine/N,N′-dimethylformamide) adduct has been used as a Vilsmeier-Haack type reagent for effective synthesis of 2-chloro-3-formyl quinolines from acetanilides under conventional and ultrasonically assisted conditions. The reaction times under sonication are quite significantly shorter than conventional methods even though the yields obtained under sonication are comparable with those obtained under reflux conditions.

Synthesis and biological evaluation of new rhodanine analogues bearing 2-chloroquinoline and benzo[h]quinoline scaffolds as anticancer agents

Several rhodanine derivatives (9-39) were synthesized for evaluation of their potential as anticancer agents. Villsmeier cyclization to synthesize aza-aromatic aldehydes, rhodanine derivatives preparation and Knoevenagel type of condensation between the rhodanines and aza-aromatic aldehydes are key steps used for the synthesis of 31 compounds. In vitro antiproliferative activity of the synthesized rhodanine derivatives (9-39) was studied on a panel of six human tumor cell lines viz. HGC, MNK-74, MCF-7, MDAMB-231, DU-145 and PC-3 cell lines. Some of the compounds were capable of inhibiting the proliferation of cancer cell lines at a micromolar concentration. Six compounds are found to be potent against HGC cell lines; compound 15 is found to be active against HGC - Gastric, MCF7 - Breast Cancer and DU145 - Prostate Cancer cell lines; compound 39 is potent against MNK-74; four compounds are found to be potent against MCF-7 cell lines; three compounds are active against MDAMB-231; nine compounds are found to be potent against DU-145; three compounds are active against PC-3 cell lines. These compounds constitute a promising starting point for the development of novel and more potent anticancer agents in future.

An efficient and facile synthesis of 2-chloro-3-formyl quinolines from acetanilides in micellar media by Vilsmeier-Haack cyclisation

Acetanilides efficiently undergo Vilsmeier Haack cyclisation in micellar media to afford 2-chloro-3-formyl quinoline derivatives in good yields. This procedure works efficiently in CTAB (cetyl trimethyl ammonium bromide), SDS (sodium dodecyl sulphate) and TX (Triton-X-100) media under reflux conditions particularly from deactivated acetanilides in good yields.