6808-65-7

Basic information

• Product Name: 2-(1,3-benzodioxol-5-yl)quinoline
• Synonyms: C10661;Dubamine;Quinoline, 2-(1,3-benzodioxol-5-yl)-
• CAS NO: 6808-65-7
• Molecular Formula: C₁₆H₁₁NO₂
• Molecular Weight: 249.264
• Mol File: 6808-65-7.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 424.2°C at 760 mmHg
• Flash Point: 153.1°C
• Density: 1.289g/cm³
• Vapor Pressure: 5.2E-07mmHg at 25°C
• Refractive Index: 1.678
• CAS DataBase Reference: 2-(1,3-benzodioxol-5-yl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-benzodioxol-5-yl)quinoline(6808-65-7)
• EPA Substance Registry System: 2-(1,3-benzodioxol-5-yl)quinoline(6808-65-7)

Safety Data

• Hazardous Substances Data: 6808-65-7(Hazardous Substances Data)

Usage

Chemical composition

Consists of a quinoline core with a 1,3-benzodioxole substituent at the 2-position.

Type of compound

Heterocyclic compound.

Potential activities

Has potential pharmacological and biological activities.

Applications

Has been studied for potential use in medicinal chemistry and drug development.

Possible uses

May be used in the treatment of various diseases and conditions.

Significance

Is an interesting target for further research and potential exploitation in the pharmaceutical industry.

Upstream product

• 120-57-0 piperonal 
• 62-53-3 aniline 
• 74-86-2 acetylene 
• 612-62-4 2-Chloroquinoline 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 69849-38-3 trimethyl(3,4-methylenedioxyphenyl)stannane 
• 109586-44-9 trifluoromethanesulfonic acid quinolin-2-yl ester 
• 853099-64-6 (E)-1-(benzo[d][1,3]dioxol-5-yl)-N-phenylmethanimine 
• 109-92-2 ethyl vinyl ether 
• 253-83-8 1,2,3-benzotriazine 
• 534-15-6 1,1-dimethoxyethane 
• 75-07-0 acetaldehyde 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 485-61-0 graveoline 
• 4179-37-7 graveolinine 

Relevant articles and documents

A Domino Heck Coupling-Cyclization-Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.

Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt

A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.