5263-17-2

Usage

InChI:InChI=1/C8H5Cl3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-5H

Upstream product

• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 104-88-1 4-chlorobenzaldehyde 
• 5333-82-4 2,2,2-trichloro-1-(4-chloro-phenyl)-ethanol 
• 63252-99-3 2,2,2-trichloro-(4-chlorophenyl)ethyl acetate 
• 683-08-9 Diethyl methylphosphonate 
• 56-23-5 tetrachloromethane 
• 52372-80-2 (4-chlorobenzylidene)hydrazine 
• 75-62-7 Bromotrichloromethane 
• 594-18-3 dibromodichloromethane 
• 52372-80-2 4-Chlorobenzaldehyde monohydrazone 
• 1620143-47-6 ethyl [2,2,2-trichloro-1-(4-chlorophenyl)ethyl]carbonate 
• 88920-83-6 2,2-Dichloro-1-(4-chloro-phenyl)-2-trimethylsilanyl-ethanol 

Downstream Products

• 33491-02-0 1-chloro-4-(chloroethynyl)benzene 
• 1256954-57-0 (Z)-benzyl 2-chloro-3-(4-chlorophenyl)acrylate 
• 1187772-36-6 2-[(4-chlorophenyl)ethynyl]benzoxazole 
• 1370422-72-2 2-{(4-chlorphenyl)ethynyl}-5-(2-pyridinyl)oxazole 
• 1005500-80-0 N-((4-chlorophenyl)ethynyl)-N,4-dimethylbenzenesulfonamide 
• 5172-02-1 1-chloro-4-(2-phenylethynyl)benzene 
• 873-73-4 4-n-chlorophenylacetylene 
• 77063-21-9 4-(4-chlorophenyl)-1,1,1-trifluorobut-3-yn-2-one 
• 10420-75-4 4'-chloroflavone 
• 60402-30-4 2-(4-chlorophenyl)-6-methyl-4H-chromen-4-one 

Relevant academic research and scientific papers

Efficient Multigram Approach to Acetylenes and CF3-ynones Starting from Dichloroalkenes Prepared by Catalytic Olefination Reaction (COR)

A novel approach to terminal acetylenes based on catalytic olefination reaction COR of arylaldehydes to form dichloroalkenes followed by treatment with nBuLi was elaborated. This method is atom economical and displays high yields and effectivity. The corresponding alkynes can be prepared in up to 97 % yield. One pot procedure towards CF3-ynones was elaborated to provide these products in up to 87 % yield starting from dichloroalkenes.

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

A Robust One-Step Approach to Ynamides

A robust one-step synthetic strategy for ynamide with cheap and easily available stock chemicals vinyl dichlorides and electron deficient amides as the starting material is described. In the absence of transition-metal catalyst, the reaction proceeds under mild reaction conditions in open air and thus rendering a convenient operation. This strategy is not only suitable for both terminal and internal ynamide synthesis but also amenable for large-scale preparation. Broad substrate scopes with respect to vinyl dichloride as well as electron-deficient amide were observed.

Ionic liquids as a reusable media for copper catalysis. Green access to alkenes using catalytic olefination reaction

It was demonstrated that ionic liquids are superb recyclable media for copper catalyzed reactions using catalytic olefination reaction as an example. As a result a novel green access to the halogenoalkenes was elaborated. Possibility to perform up to five reaction cycles without catalyst leaching and decreasing of the yield was demonstrated. A number of various ionic liquids was screened and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim] [BF4]) was found the solvent with highest efficiency. Mild conditions, high atom economy comparing to other known methods, low amounts of wastes and possibility to recover ionic liquid are the advantages of the proposed method.

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

Cu and Au nanocomposites in catalytic olefination reaction

Metal-vapor synthesis-prepared Cu, Ag, Au and bimetallic Au-Cu (optimal) nanocomposites catalyse olefination of hydrazones with polyhalomethanes.

Pd0-Catalyzed carbonylation of 1,1-dichloro-1-alkenes, a new selective access to Z-α-chloroacrylates

A novel and fully chemo- and stereoselective three component strategy leading to Z-α-chloroacrylates by a Pd0-catalyzed reaction of CO (1 atm) with 1,1-dichloro-1-alkenes and various alcohols is disclosed. This catalytic approach compares favourably with the Wittig type strategies as α-chloroacrylates of pure Z configuration are obtained in high yield. The Royal Society of Chemistry.

Effect of the catalyst nature and quantity on catalytic olefination

The study of the catalyst nature effect on the catalytic olefination of 4-chlorobenzaldehyde hydrazone by polyhaloalkanes revealed that the best catalysts for the reaction are copper salts. With polyhaloalkanes more active than CCl4, like CBrs

Catalytic olefination. Estimation of the reactivity of polyhaloalkanes

Global electrophilicity indices and carbon-halogen bond energies of a wide series of halogen derivatives were calculated in terms of the density functional theory (DFT). The calculated values were used to estimate the reactivity of halogen derivatives under conditions of catalytic olefination. Reactions of N-unsubstituted hydrazones with polyhaloalkanes in the presence of CuCl afforded substituted alkenes. The relation between the structure of polyhaloalkanes and their reactivity was studied using the reaction with 4-chlorobenzaldehyde hydrazone as an example. It was found that increase in the global electrophilicity index and decrease in the C-Hlg bond energy are accompanied by increase in the olefinating power of halogen derivatives.

SmI2-mediated elimination reaction of trichloromethyl carbinols: A facile method to synthesize vinyl dichlorides

Samarium diiodide-mediated elimination reaction provides a simple and general method to synthesize vinyl dichlorides from trichloromethyl carbinols directly in good to excellent yields.