68236-25-9

Basic information

• Product Name: 2-CHLORO-5,6,7-TRIMETHOXY-QUINOLINE-3-CARBALDEHYDE
• Synonyms: 2-CHLORO-5,6,7-TRIMETHOXY-3-QUINOLINECARBALDEHYDE;2-CHLORO-5,6,7-TRIMETHOXY-QUINOLINE-3-CARBALDEHYDE;OTAVA-BB 1045296
• CAS NO: 68236-25-9
• Molecular Formula: C₁₃H₁₂ClNO₄
• Molecular Weight: 281.69
• Mol File: 68236-25-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 418.5°C at 760 mmHg
• Flash Point: 206.9°C
• Appearance: /
• Density: 1.326g/cm³
• Vapor Pressure: 3.26E-07mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 2-CHLORO-5,6,7-TRIMETHOXY-QUINOLINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5,6,7-TRIMETHOXY-QUINOLINE-3-CARBALDEHYDE(68236-25-9)
• EPA Substance Registry System: 2-CHLORO-5,6,7-TRIMETHOXY-QUINOLINE-3-CARBALDEHYDE(68236-25-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 68236-25-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 2045, 1978 DOI: 10.1016/S0040-4039(01)94745-8

InChI:InChI=1/C13H12ClNO4/c1-17-10-5-9-8(11(18-2)12(10)19-3)4-7(6-16)13(14)15-9/h4-6H,1-3H3

Upstream product

• 24313-88-0 3,4,5-Trimethoxyaniline 
• 4304-24-9 N-(3,4,5-trimethoxyphenyl)acetamide 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 95395-37-2 (Z)-3-Phenylamino-2-(2,5,6,7-tetramethoxy-quinolin-3-ylmethyl)-acrylonitrile 
• 95395-34-9 (Z)-3-Phenylamino-2-(5,6,7-trimethoxy-quinolin-3-ylmethyl)-acrylonitrile 

Relevant articles and documents

Synthesis, structure-activity relationship and molecular docking studies of novel quinoline-chalcone hybrids as potential anticancer agents and tubulin inhibitors

A new series of quinoline-chalcone hybrids was synthesized. The structures of these compounds were characterized by spectroscopic methods including 1H and 13CNMR and mass spectroscopy. The cytotoxic activity of compounds was evaluated against four human cancer cell lines including A2780 (human ovarian carcinoma) and A2780/RCIS (Cisplatin resistant human ovarian carcinoma), MCF-7 (human breast cancer cells), MCF-7/MX (Mitoxantrone resistant human breast cancer cells) and normal Huvec cells. The structure-activity relationship of synthesized compounds is discussed. Among quinolines 5e, 5g and 5j possessing benzoyl group showed significant cytotoxic activity against both resistant cancer cells and their parents. Compounds 5g and 5j, demonstrated the most antiproliferative activity with IC50 values ranging from 2.32 to 22.4 μM. They were also identified as tubulin inhibitors and induced cell cycle arrest at G2/M phase and apoptosis. Compound 5j induced more arrest at G2/M phase in four cancer cell lines compared to compound 5g. Finally, molecular dynamics simulation and molecular docking studies of compound 5j into the colchicine-binding site of tubulin demonstrated the possible interaction of this compound in the active site of tubulin.

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 5. The Synthesis of 2-Chloroquinoline-3-carbaldehydes

Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution.The reaction is shown to involve successive conversion of the acetanilide into an imidoyl chloride and then an N-(α-chlorovinyl)aniline.The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde.The diformylated intermediates may be isolated in several cases and separately cyclised with polyphosphoric acid.