873-31-4

Usage

Uses

Used in Pharmaceutical Industry:
1-Chloro-2-ethynylbenzene is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows for the formation of diverse molecular frameworks, which can be further functionalized to develop new drugs with improved therapeutic properties.
Used in Chemical Synthesis:
1-Chloro-2-ethynylbenzene is used as a key building block in the synthesis of complex organic molecules. Its reactivity allows for various chemical transformations, such as cross-coupling reactions, which can be employed to construct a wide range of organic compounds with potential applications in various fields.
Used in the Synthesis of 4-(2-chlorophenylethynyl)-3-methyl-5-phenylisoxazole:
1-Chloro-2-ethynylbenzene is used as a starting material for the synthesis of 4-(2-chlorophenylethynyl)-3-methyl-5-phenylisoxazole, a compound with potential applications in various fields, such as materials science and pharmaceuticals. The ethynyl group in 1-chloro-2-ethynylbenzene can be utilized in a cycloaddition reaction to form the isoxazole ring, leading to the desired product.

InChI:InChI=1/C8H5Cl/c1-2-7-5-3-4-6-8(7)9/h1,3-6H

Upstream product

• 56772-79-3 1-(2,2-dichlorovinyl)-2-chlorobenzene 
• 89-98-5 2-chloro-benzaldehyde 
• 68089-86-1 chloromethyl(triphenyl)phosphonium iodide 
• 105273-33-4 1-chloro-2-(trimethylsilylethynyl)benzene 
• 24654-08-8 3-(2-chlorophenyl)prop-2-ynoic acid 
• 108-90-7 chlorobenzene 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 694-80-4 2-bromo-1-chlorobenzene 
• 401514-40-7 1-chloro-2-(2,2-dibromovinyl)benzene 
• 19819-95-5 2-(2-chlorophenyl)-1-ethanol 
• 615-41-8 2-iodochlorobenzene 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 

Downstream Products

• 115077-35-5 2-(2-chlorophenyl)-3-(trimethylsilyl)-(E)-prop-2-enenitrile 
• 115077-34-4 2-(2-chlorophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile 
• 80114-95-0 (3S,5S,8R,9S,10S,13R,14S,17R)-3-(2-Chloro-phenylethynyl)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 80114-98-3 (3R,5S,8R,9S,10S,13R,14S,17R)-3-(2-Chloro-phenylethynyl)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 110296-06-5 (Z)-2-chlorostyryl phenyl telluride 
• 80221-17-6 1,4-bis(o-chlorophenyl)buta-1,3-diyne 
• 10271-57-5 1-chloro-2-(2-phenylethynyl)benzene 
• 479546-79-7 N-[6-(2-chloro-phenylethynyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethyl-propionamide 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 873961-52-5 2-((2-chlorophenyl)ethynyl)benzaldehyde 
• 105273-33-4 1-chloro-2-(trimethylsilylethynyl)benzene 

Relevant academic research and scientific papers

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

Design, Synthesis, and in vitro Evaluation of P2X7 Antagonists

The P2X7 receptor is a promising target for the treatment of various diseases due to its significant role in inflammation and immune cell signaling. This work describes the design, synthesis, and in vitro evaluation of a series of novel derivatives bearing diverse scaffolds as potent P2X7 antagonists. Our approach was based on structural modifications of reported (adamantan-1-yl)methylbenzamides able to inhibit the receptor activation. The adamantane moieties and the amide bond were replaced, and the replacements were evaluated by a ligand-based pharmacophore model. The antagonistic potency of the synthesized analogues was assessed by two-electrode voltage clamp experiments, using Xenopus laevis oocytes that express the human P2X7 receptor. SAR studies suggested that the replacement of the adamantane ring by an aryl-cyclohexyl moiety afforded the most potent antagonists against the activation of the P2X7 cation channel, with analogue 2-chloro-N-[1-(3-(nitrooxymethyl)phenyl)cyclohexyl)methyl]benzamide (56) exhibiting the best potency with an IC50 value of 0.39 μΜ.

One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines to Access 2,3-Dihydro-1 H-imi-dazo[1,2-a]indoles

A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1 H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C-N bonds are constructed- by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.

Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes

The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives

A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.

Efficient synthesis of N-arylsulfonyl-1,2,3-triazoles from 1,1-dibromo-2-arylethylenes

N-arylsulfonyl-1,2,3-triazoles were synthesized from 1,1-dibromo-2-arylethylenes via a one-pot reaction involving the Cs2CO3-mediated dehydrobromination process of the dibromoalkenes to produce alkynes followed by the Cu(I)-catalyzed Huisgen cycloaddition of the alkyne intermediates with tosyl azide.

Synthesis of 1-arylsulfonyl-1,2,3-triazoles from (Z)-arylvinyl bromides by sequential elimination–cycloaddition reaction

[Figure not available: see fulltext.]Efficient synthesis of 1-arylsulfonyl-1,2,3-triazoles from easily available (Z)-arylvinyl bromides is described. The sequential reaction involves elimination of HBr from (Z)-arylvinyl bromides promoted by KOH and copper-catalyzed (3+2) cycloaddition reaction between the alkyne intermediates and sulfonyl azides.

Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization

(Chemical Equation Presented) Mild and direct C-H bond functionalizations and vinylations of tetrahydrofuran with alkynes have been accomplished through visible light photocatalysis, yielding a range of vinyl tetrahydrofurans under the synergistic actions of organic dye-type photocatalyst eosin Y, tert-butyl hydroperoxide (t-BuOOH), and a 45 W household lightbulb. A significant kinetic isotope effect (KIE) was recorded, which helps shed light on the mechanistic course.