1000782-65-9

Basic information

• Product Name: 2-CHLORO-3-ETHYNYLQUINOLINE
• Synonyms: 2-CHLORO-3-ETHYNYLQUINOLINE
• CAS NO: 1000782-65-9
• Molecular Formula: C11H6ClN
• Molecular Weight: 187.62504
• Mol File: 1000782-65-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-CHLORO-3-ETHYNYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-3-ETHYNYLQUINOLINE(1000782-65-9)
• EPA Substance Registry System: 2-CHLORO-3-ETHYNYLQUINOLINE(1000782-65-9)

Safety Data

• Hazardous Substances Data: 1000782-65-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-ethynylquinoline is used as a key intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and diverse biological activities.
Used in Agrochemical Industry:
2-Chloro-3-ethynylquinoline is used as a building block in the development of agrochemicals, contributing to its antimicrobial properties for crop protection.
Used in Drug Discovery Research:
2-Chloro-3-ethynylquinoline is employed as a valuable compound in drug discovery research due to its antimicrobial, anti-inflammatory, and anticancer properties, making it a promising candidate for the development of novel therapeutic agents.
Used in Novel Drug Design:
2-Chloro-3-ethynylquinoline serves as a crucial component in the design of new drugs and biologically active compounds, leveraging its unique chemical structure and potential for further functionalization.

Upstream product

• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 558-13-4 carbon tetrabromide 

Relevant articles and documents

The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity

The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.

Synthesis of an indole containing KDR kinase inhibitor by tandem Sonogashira coupling-5-endo-dig-cyclization as a key step

An efficient synthesis of the potent KDR kinase inhibitor 3-[5-[[4-(methylsulfonyl)-1-piperazinyl]methyl]-1H-indol-2-yl]quinoline-2-(1H)-one using a Sonogashira coupling-5-endo-dig-cyclization strategy is described.

DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes

Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).

Na2S-mediated synthesis of terminal alkynes from: Gem -dibromoalkenes

The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed. Various precursors derived from heteroaromatic/aromatic/aliphatic aldehydes were found compatible. The reaction is proposed to proceed through the Fritsch-Buttenberg-Wiechell (FBW) rearrangement involving the corresponding vinyl carbene. Using mild reaction conditions with inexpensive Na2S·9H2O under air atmosphere has significant advantages over earlier routes.