78593-41-6

Basic information

• Product Name: 6-ETHYNYL-QUINOLINE
• Synonyms: 6-ETHYNYL-QUINOLINE
• CAS NO: 78593-41-6
• Molecular Formula: C₁₁H₇N
• Molecular Weight: 153.17998
• Mol File: 78593-41-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 49-50 °C(Solv: hexane (110-54-3))
• Boiling Point: 282.4±13.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.33±0.10(Predicted)
• CAS DataBase Reference: 6-ETHYNYL-QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ETHYNYL-QUINOLINE(78593-41-6)
• EPA Substance Registry System: 6-ETHYNYL-QUINOLINE(78593-41-6)

Safety Data

• Hazardous Substances Data: 78593-41-6(Hazardous Substances Data)

Usage

General Description

6-Ethynylquinoline is a chemical compound with the molecular formula C11H7N. It is a yellow, crystalline solid that is commonly used in organic synthesis and the development of fluorescent dyes, luminophores, and chemosensors. Its structure consists of a benzene ring fused with a pyridine ring, with an ethynyl group attached to the carbon atom in the 6-position of the pyridine ring. 6-Ethynylquinoline has been studied for its potential applications in medical imaging, optical materials, and pharmaceuticals. It has also been used as a fluorescent probe in biological and biochemical research due to its unique optical properties.

Upstream product

• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 135808-70-7 1-(quinolin-6-yl)butan-1-one 
• 13327-31-6 6-iodoquinoline 
• 1066-54-2 trimethylsilylacetylene 
• 5332-25-2 6-bromoquinoline 
• 683774-32-5 6-trimethylsilylethynylquinoline 
• 78593-36-9 2-Methyl-4-quinolin-6-yl-but-3-yn-2-ol 

Downstream Products

• 23395-72-4 quinoline-6-carbonitrile 

Relevant articles and documents

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products

Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

Direct synthesis of α-trifluoromethyl ketone from (hetero)arylacetylene: Design, intermediate trapping, and mechanistic investigations

Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This metho