27951-92-4

Basic information

• Product Name: 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]quinoline
• Synonyms: 2-(2-(1,3-Benzodioxol-5-yl)vinyl)quinoline; 2-[(E)-2-(1,3-Benzodioxol-5-yl)vinyl]quinoline; Quinoline, 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-
• CAS NO: 27951-92-4
• Molecular Formula: C₁₈H₁₃NO₂
• Molecular Weight: 275.3013
• Mol File: 27951-92-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 447°C at 760 mmHg
• Flash Point: 160.6°C
• Density: 1.303g/cm³
• Vapor Pressure: 9.19E-08mmHg at 25°C
• Refractive Index: 1.746
• CAS DataBase Reference: 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]quinoline(27951-92-4)
• EPA Substance Registry System: 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]quinoline(27951-92-4)

Safety Data

• Hazardous Substances Data: 27951-92-4(Hazardous Substances Data)

Usage

Derivative of quinoline

Heterocyclic aromatic organic compound This compound is derived from quinoline, which is a heterocyclic aromatic organic compound consisting of a benzene ring fused with a nitrogen-containing pyridine ring.

1,3-benzodioxol-5-yl group

Specific chemical properties and biological activities The presence of this group in the molecule imparts specific chemical properties and biological activities, such as antifungal and antibacterial properties.

Pharmacological and biological activities

Antifungal and antibacterial properties 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]quinoline has been studied for its potential pharmacological and biological activities, including its ability to combat fungi and bacteria.

Potential application

Medicinal chemistry and drug development The compound has been investigated for its potential use in the development of new drugs and its application in medicinal chemistry.

Subject of interest

Pharmaceutical and biotechnology industries Due to its unique chemical structure and properties, 2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]quinoline is of interest for further research and potential applications in various fields, including the pharmaceutical and biotechnology industries.

Upstream product

• 91-63-4 2-methylquinoline 
• 120-57-0 piperonal 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 5344-90-1 2-Aminobenzyl alcohol 
• 22214-31-9 (E)-4-(benzo[d][1,3]dioxol-5-yl)but-3-en-2-one 
• 93-10-7 quinoline-2-carboxylic acid 
• 4491-33-2 ethyl quinoline-2-carboxylate 
• 5470-96-2 quinoline 2-carbaldehyde 
• 58005-36-0 (benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 495-76-1 piperonol 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 552-89-6 2-nitro-benzaldehyde 
• 772-03-2 2-vinylquinoline 

Downstream Products

• 375395-24-7 2-(2-(benzo[d][1,3]-dioxol-5-yl)ethyl)-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Water-Sculpting of a Heterogeneous Nanoparticle Precatalyst for Mizoroki-Heck Couplings under Aqueous Micellar Catalysis Conditions

Powdery, spherical nanoparticles (NPs) containing ppm levels of palladium ligated by t-Bu3P, derived from FeCl3, upon simple exposure to water undergo a remarkable alteration in their morphology leading to nanorods that catalyze Mizoroki-Heck (MH) couplings. Such NP alteration is general, shown to occur with three unrelated phosphine ligand-containing NPs. Each catalyst has been studied using X-ray photoelectron spectroscopy (XPS), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), and cryogenic transmission electron microscopy (cryo-TEM) analyses. Couplings that rely specifically on NPs containing t-Bu3P-ligated Pd occur under aqueous micellar catalysis conditions between room temperature and 45 °C, and show broad substrate scope. Other key features associated with this new technology include low residual Pd in the product, recycling of the aqueous reaction medium, and an associated low E Factor. Synthesis of the precursor to galipinine, a member of the Hancock family of alkaloids, is suggestive of potential industrial applications.

Copper-catalyzed asymmetric silyl addition to alkenyl-substituted N -heteroarenes

Asymmetric conjugate addition of PhMe2SiBPin to a wide range of N-heteroaryl alkenes proceeded in the presence of a copper catalyst coordinated with an easily accessible chiral phosphoramidite ligand to afford useful β-silyl N-heteroarenes in high yields (up to 96%) and excellent enantioselectivities (up to 97% ee).

NaCl as Catalyst and Water as Solvent: Highly E-Selective Olefination of Methyl Substituted N-Heteroarenes with Benzyl Amines and Alcohols

Oxidative coupling of benzylamines and alcohols with methyl substituted N-heteroarenes such as quinolines and quinoxalines has been achieved using chloride, a sea abundant anion as the catalyst for practical synthesis of a wide range of E-disubstituted olefins in aqueous medium. Detailed mechanistic studies and control experiments were carried out to deduce the reaction mechanism which indicated that in situ formed ClO2- is the active form of the catalyst. We have successfully carried out a 1 g scale reaction using this methodology, and five pharmaceutically relevant conjugated olefins were also synthesized by this method in moderate to good yields.