10271-57-5

Usage

Type of compound

Alkyne

Structural features

Contains a triple bond between two carbon atoms, one of which is connected to a phenyl group and the other to a 2-chlorophenyl group

Uses

Organic synthesis, pharmaceutical research (building block for creating more complex molecules)

Reactivity

High (due to the presence of the triple bond, useful in forming carbon-carbon bonds in chemical reactions)

Synthesis methods

Various methods available

Importance

An important intermediate in the production of many pharmaceuticals and other organic compounds

InChI:InChI=1/C14H9Cl/c15-14-9-5-4-8-13(14)11-10-12-6-2-1-3-7-12/h1-9H

Upstream product

• 105273-35-6 1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-ethoxy)-ethanesulfonic acid 2-chloro-phenyl ester 
• 536-74-3 phenylacetylene 
• 13146-23-1 copper(I) phenylacetylenide 
• 615-41-8 2-iodochlorobenzene 
• 591-50-4 iodobenzene 
• 873-31-4 2-chlorophenylacetylene 
• 95-50-1 1,2-dichloro-benzene 
• 694-80-4 2-bromo-1-chlorobenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 104581-35-3 1-(2-Chloro-phenylethynyl)-cyclohexanol 
• 20109-09-5 1-(phenylethynyl)-1-cyclohexanol 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 95-51-2 o-chloroaniline 

Downstream Products

• 10271-59-7 1-(o-Chlorphenyl)-2-phenylhexen 
• 42951-53-1 1-(n-octyl)-2-phenyl-1H-indole 
• 18434-11-2 1-n-hexyl-2-phenyl-1H-indole 
• 52604-15-6 1-benzyl-2-phenyl-1H-indole 
• 18434-12-3 1,2-diphenyl-1H-indole 
• 1657-51-8 (Z)-1-chloro-2-styrylbenzene 
• 57479-60-4 1-phenyl-2-(2-chlorophenyl)ethanone 
• 72867-72-2 1-(2-chlorophenyl)-2-phenyl-1-ethanone 
• 85-01-8 phenanthrene 
• 452094-35-8 C₅H₄NCHCSn(C₄H₉)3C₆H₄(o-Cl) 
• 1072190-43-2 phenyl-(2-phenyl-indol-1-yl)carbamic acid tert-butyl ester 
• 1095510-53-4 3-benzyl-2-cyclohexyl-2H-indazole 

Relevant academic research and scientific papers

Pd nanoparticles immobilized on poly(NIPAM-co-4-VP) hydrogel: Highly active and reusable catalyst for carbon-carbon coupling reactions in water

Poly(N-isopropylacrylamide-co-4-vinylpyridine) [poly(NIPAM-co-4-VP)] co-polymer exhibited inverse temperature solubility with a lower critical solution temperature (LCST) in water. Pd nanoparticles were immobilized on these poly(NIPAM-co-4-VP) hydrogels. The heterogeneous Pd catalyst showed high catalytic activities for carbon-carbon coupling reactions, such as Suzuki-Miyaura, Heck-Mizoroki, and Sonogashira coupling reactions in water. The Pd catalyst immobilized on poly(NIPAM-co-4-VP) hydrogel (NIPAM:4-VP = 1:1 M ratio) showed an excellent recyclability and excellent yield for carbon-carbon coupling reactions.

Sonogashira cross-coupling of arenediazonium salts

(Figure Presented) Star-crossed lovers: The domino iododediazoniation/ Sonogashira cross-coupling of terminal alkynes with arenediazonium salts has been developed. The arenediazonium salt synthesis/iododediazoniation/Sonogashira cross-coupling sequence can also be performed as a one-pot process, omitting the isolation of the arenediazonium salt.

Encapsulating palladium nanoparticles inside ethylenediamine functionalized and crosslinked chlorinated poly(vinyl chloride) nanofibers as an efficient and stable heterogeneous catalyst for coupling reactions

Palladium chloride and chlorinated poly (vinyl chloride) (CPVC) mixture were prepared into homogeneous solution, followed by electrospinning to make uniform nanofibers with average diameter of ~460 nm. Then, these composite nanofibers were treated in ethy

(BeDABCO)2Pd2Cl6 as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction

An efficient catalytic system using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2] octane chloride and palladium chloride ((BeDABCO)2Pd 2Cl6) was developed for the Sonogashira reaction. In the presence of a catalytic amount of this efficient, stable homogeneous catalytic system that is non-sensitive to air and moisture, various aryl halides were efficiently coupled with phenylacetylene in good yields in H2O at 50C under copper-free conditions. Benzyl dabco as an efficient ligand and also a quaternary ammonium salt had an efficient stabilizing effect on the Pd(0) species. Copyright

The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder

The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder has been developed; terminal alkynes couple with aryl, alkenyl iodide and aryl bromide in the presence of cuprous iodide, triphenylphosphine, potassium hydroxide and ultrafine particle nickel(0) to provide the corresponding cross-coupling products with high yields.

Tandem Sonogashira coupling: An efficient tool for the synthesis of diarylalkynes

(Chemical Equation Presented) The tandem Sonogashira coupling reaction of aryl halides provides an efficient method for the synthesis of diarylalkynes. Several aryl halides were coupled with 2-methyl-3-butyn-2-ol as acetylene source in the presence of PdCl2(PPh3)2 and CuI. Following the deprotection of the acetylene moiety in the same pot using a strong base, the Sonogashira coupling of a second aryl halide led to the formation of the appropriate diarylakyne. The established protocoll was successfully extended to the preparation of compound libraries.

DBU-Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1-Dibromoalkenes at Room Temperature

The reaction of 1,1-dibromoalkenes and aryl iodides in the presence of DBU and a PdII/CuI catalytic system afforded diaryl alkynes and enynes at ambient temperature. Control experiments demonstrated the essential ligand role of DBU i

Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes

Carbon-carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C-C cross-coupling reaction of two kinds of organic halide, a gem -dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination-hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

Copper- and phosphine-free Sonogashira coupling reaction catalyzed by silica-(acac)-supported palladium nanoparticles in water

A palladium-based catalyst supported on acac-functionalized silica was used as a heterogeneous catalyst for the Sonogashira cross-coupling reaction of various aryl halides and phenylacetylene under copper- and phosphine-free conditions. This catalytic sys

Visible light-mediated gold-catalysed carbon(sp2)-carbon(sp) cross-coupling

A dual photoredox and gold-catalysed cross-coupling reaction of alkynyltrimethylsilanes and aryldiazonium tetrafluoroborates is described. The reaction proceeds through visible-light mediated oxidative addition of aryldiazoniums, transmetalation of alkynyltrimethylsilanes and aryl-alkynyl reductive elimination. Exclusive selectivity for silyl-substituted alkynes is observed, with no reactivity observed for terminal alkynes.