14309-60-5

Usage

Physical state

Colorless liquid

Usage

Manufacturing of pharmaceuticals, dyes, and other chemicals

Application in synthesis

Building block in organic synthesis, reagent in the preparation of various organic compounds

Hazard

Flammable, should be handled with care

Consumer product usage

Not widely used, but commonly used in research and industrial applications

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 108842-08-6 α,α'-dibromo-2-methyl-bibenzyl 
• 95-46-5 2-methylphenyl bromide 
• 7664-41-7 ammonia 
• 629-05-0 n-octyne 
• 95-49-8 2-methylchlorobenzene 
• 32584-71-7 diphenyl(phenylethynyl)stibine 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 131-58-8 2-Methylbenzophenone 
• 54737-45-0 (E)-2-bromostilbene 
• 54737-46-1 2,α,α'-tribromo-bibenzyl 
• 209287-67-2 tris(o-tolyl)antimony diacetate 

Downstream Products

• 4505-48-0 2-phenylindene 
• 144694-49-5 1-(2-methylphenyl)-2-phenylacenaphthylene 
• 117482-13-0 4-methyl-2-phenyl-indan-1-one 
• 117482-14-1 2-(o-tolyl)-2,3-dihydro-1H-inden-1-one 
• 53423-25-9 1-methyl-2[(1Z)-2-phenylethenyl]benzene 
• 5033-67-0 2-(2-methylphenyl)-1-phenyl-1-ethanone 
• 205529-06-2 Diphenyl-((E)-1-phenyl-2-o-tolyl-vinyl)-phosphane 
• 53423-25-9 (E)-1-methyl-2-styryl-benzene 
• 452094-47-2 CH₃C₆H₄CSn(C₄H₉)3CHC₆H₅ 
• 452094-47-2 C₅H₄NCHCSn(C₄H₉)3C₆H₄(o-CH₃) 
• 16216-14-1 o-methylbenzil 

Relevant academic research and scientific papers

Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions

PdCl2(PPh3)2 combined with TBAF under solvent-free conditions provided general and fast Sonogashira cross-coupling reactions of aryl halides with terminal alkynes. In particular, this protocol could be applied to the reactions of deactivated aryl chlorides. In the presence of 3 mol % of PdCl2(PPh3)2 and 3 equiv of TBAF, a number of ArX species (X = I, Br, Cl) were coupled with alkynes to afford the corresponding products in moderate to excellent yields under copper-, amine-, and solvent-free conditions.

Palladium immobilized on amidoxime-functionalized magnetic Fe3O4 nanoparticles: A highly stable and efficient magnetically recoverable nanocatalyst for sonogashira coupling reaction

We describe the synthesis of a novel Fe3O4/amidoxime (AO)/Pd nanocatalyst by grafting of AO groups on Fe3O4 nanoparticles and subsequent deposition of Pd nanoparticles. Prior to grafting of AO, the 2-cyanoethyl-

Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira-Hagihara coupling reactions

Pd(0) nanoparticles supported on modified crosslinked polystyrene were synthesized and characterized. Crosslinked polystyrene was reacted with trioxane and chlorotrimethylsilane in the presence of SnCl4 to form Merrifield resin. The Merrifield

Poly(vinylpyridine)-grafted silica containing palladium or nickel nanoparticles as heterogeneous catalysts for the Sonogashira coupling reaction

Efficient catalytic systems based on palladium and nickel nanoparticles supported on poly(4-vinylpyridine) (P4VPy)-grafted silica were prepared. After preparation of P4VPy-grafted silica, complexation with PdCl2 and NiCl2 was carried

Copper-free sonogashira coupling in water with linear polystyrene- stabilized PdO nanoparticles

Linear polystyrene-stabilized PdO nanoparticles generated by thermal decomposition of palladium acetate have high catalytic activity for Sonogashira coupling in water under copper-free conditions. The catalyst was recovered and reused at least four times

A versatile catalyst for the sonogashira coupling of aryl chlorides

Aryl chlorides are suitable substrates for the Sonogashira coupling! By using the versatile catalyst system Na2[PdCl4]/PR3/ Cul (PR3= (1-Ad)2PBn, PtBu3), the Sonogashira coupling [Eq. (a)] of aryl chlorides with alkynes generates excellent yields of the corresponding disubstituted aryl alkynes.

Efficient and copper-free sonogashira cross-coupling reaction catalyzed by Pd(OAc)2/pyrimidines catalytic system

An efficient and copper-free catalyst system for Sonogashira cross-coupling reaction is presented. In the presence of 3 mol-% of Pd(OAc)2 and 6 mol-% of 2-aminopyrimidine-4,6-diol, various aryl iodides and bromides can be coupled smoothly with

Copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3-diene catalyzed sonogashira cross-coupling of aryl halides with terminal alkynes under aerobic and solvent-free conditions

The Sonogashira cross-coupling of aryl halides with terminal alkynes catalyzed by an inexpensive copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3- diene [Cu(OAc)2/DAB-Ph] catalytic system is reported. A series of ligands, including diazabutadiene systems, N,N-dimethylglycine, L-proline, ethylenediamine, and phosphines, were evaluated, and 1,4-diphenyl-1,4-diazabuta- 1,3-diene provided the best results. In the presence of copper(II) acetate (10 mol%), 1,4-diphenyl-1,4-diazabuta-1,3-diene (20 mol%), and tetrabutylammonium fluoride (3 equiv), a number of aryl iodides or bromides were treated smoothly with alkynes to afford the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under aerobic and solvent-free conditions. Georg Thieme Verlag Stuttgart.

Efficient sonogashira coupling reaction catalyzed by palladium(II) β-oxoiminatophosphane complexes under mild conditions

Palladium(II) β-oxoiminatophosphane complexes were used as catalysts for the Sonogashira coupling reaction. In the presence of very low amounts of the complexes, various aryl iodides and bromides were efficiently coupled with phenylacetylene even at room

Phosphine-free Sonogashira coupling: reactions of aryl halides catalysed by palladium(II) complexes of azetidine-derived polyamines under mild conditions

Readily synthesised, water-stable pyridylazetidine-based Pd(II) complexes have been studied as catalysts for the Sonogashira coupling reaction. Under low catalyst loadings, various aryl bromides and chlorides were efficiently coupled with phenylacetylene