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

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

Uses

Used in Organic Synthesis:
6-Ethynylquinoline is used as a key intermediate in the synthesis of various organic compounds, particularly those with potential applications in pharmaceuticals and materials science. Its ethynyl group allows for further functionalization and the creation of a diverse range of derivatives.
Used in Fluorescent Dyes and Lumophores:
6-Ethynylquinoline is utilized as a building block for the development of fluorescent dyes and luminophores, which are essential in the creation of advanced optical materials and devices. These dyes and luminophores can be used in various applications, including sensors, imaging, and lighting technologies.
Used in Chemosensors:
As a component in chemosensors, 6-Ethynylquinoline contributes to the detection and measurement of specific chemical species. Its unique structure and properties make it suitable for the design of sensors with high selectivity and sensitivity.
Used in Medical Imaging:
6-Ethynylquinoline has been studied for its potential use in medical imaging, where it could enhance the visualization of biological processes and structures. Its fluorescent properties could be harnessed to improve diagnostic techniques and monitor disease progression.
Used in Pharmaceutical Development:
6-Ethynylquinoline is employed as a starting material or a structural component in the development of new pharmaceuticals. Its unique chemical and optical properties may contribute to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used as a Fluorescent Probe in Biological and Biochemical Research:
6-Ethynylquinoline serves as a valuable fluorescent probe in biological and biochemical research, enabling the study of cellular processes, molecular interactions, and the behavior of biological systems. Its optical properties allow for the tracking and visualization of specific biomolecules and cellular events.

Upstream product

• 13327-31-6 6-iodoquinoline 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 135808-70-7 1-(quinolin-6-yl)butan-1-one 
• 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.

SMALL MOLECULE INHIBITION OF SULFOTRANSFERASE SULT1A3

Provided herein are small molecule compounds and methods inhibiting human sulfotransferase 1A3 (SULT1A3) using these small molecule compounds. Methods of manufacturing and treatment are also disclosed.

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).

One-pot synthesis of 1,3-enynes with a CF3 group on the terminal sp2 carbon by an oxidative Sonogashira cross-coupling reaction

Oxidative Sonogashira cross-coupling reactions of (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane with arylacetylene were achieved using silver fluoride and a palladium catalyst, to afford high yields of various 1,3-enynes with a CF3 group on the terminal sp2 carbon. Silver fluoride promoted C-Si bond dissociation and oxidation of palladium, enabling catalytic use of palladium.

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

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Synthesis of 1-hetarylethylphosphonates

Previously unknown potentially biologically active diethyl 1-(pyridin-3-yl)-, 1-(quinolin-3-yl)-, and 1-(quinolin-6-yl)ethylphosphonates were synthesized by palladium-catalyzed reduction of the corresponding α,β-unsaturated precursors with ammonium formate. The reduction of diethyl 1-(quinolin-6-yl)ethenylphosphonate was accompanied by formation of diethyl 1-(1,2,3,4-tetrahydroquinolin-6-yl)ethylphosphonate as by-product.

Hydrophosphorylation of terminal alkynes catalyzed by palladium

A series of new 1-aryl-, 1-heteroaryl-, and 1-alkylethenylphosphonates was prepared by hydrophosphorylation of terminal acetylenes catalyzed by palladium. A stable in air complex Pd2(dba)3·CHCl3 was applied as catalyst. The reaction mechanism is discussed.