4289-20-7

Usage

Purity

97%

Physical state

Colorless liquid

Molecular weight

142.2 g/mol

Class

Alkynes (unsaturated hydrocarbons with a carbon-carbon triple bond)

Uses

Building block in the synthesis of various organic compounds, production of pharmaceuticals, agrochemicals, and other fine chemicals, reagent in organic synthesis, solvent in various chemical processes.

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 106-95-6 allyl bromide 
• 536-74-3 phenylacetylene 
• 107-05-1 3-chloroprop-1-ene 
• 6088-96-6 (penta-1,4-diynyl)benzene 
• 57718-13-5 (5-bromo-pent-1-ynyl)-benzene 
• 13146-23-1 copper(I) phenylacetylenide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1745-31-9 allyl vinylacetate 
• 556-56-9 allyl iodid 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 557-40-4 Allyl ether 
• 6928-78-5 Bis(phenylethynyl)magnesium 
• 591-87-7 Allyl acetate 

Downstream Products

• 3240-29-7 1-Phenylpent-4-en-1-one 
• 34600-24-3 1-Phenyl-3-methyl-4-penten-1-yne 
• 34600-27-6 3,3-dimethyl-5-phenylpent-1-en-4-yne 
• 34600-28-7 (3-Vinyl-hept-1-ynyl)-benzene 
• 31508-14-2 penta-1,2,4-trien-1-ylbenzene 
• 31552-04-2 (Z)-1-phenyl-3-penten-1-yne 
• 120255-11-0 6-Allyl-7-methoxy-2-methyl-5-phenyl-benzofuran-4-ol 
• 120255-09-6 (4S,5S)-5-Allyl-2-methyl-4-phenyl-4,5-dihydro-cyclopenta[b]furan-6-one 
• 120255-09-6 (4S,5R)-5-Allyl-2-methyl-4-phenyl-4,5-dihydro-cyclopenta[b]furan-6-one 
• 122603-36-5 C₁₃H₁₆ 
• 97632-25-2 (Z)-penta-1,4-dien-1-ylbenzene 
• 1159211-37-6 [(1Z)-(1,2-2H₂)penta-1,4-dien-1-yl]benzene 
• 1119899-80-7 B₁₀H₁₀C₂CH₂CH(C₅H₄N)C(CH₂CHCH₂)C(C₆H₅) 
• 1186623-43-7 C₂₁H₂₀O₂ 

Relevant academic research and scientific papers

Regio- and Stereoselective Synthesis of 3,6-Dien-1-ynes by Nickel-Catalyzed Coupling Reaction of Allyl Chlorides, 1-Alkynes, and Alkynyltins

In the presence of a nickel catalyst prepared from Ni(acac)2 and DIBALH (1/1) in situ, three-component coupling reaction of allyl chlorides, 1-alkynes, and alkynyltins yielded regio- and stereoselective 3,6-dien-1-ynes in THF.

Sp-sp3 Coupling reactions of alkynylsilver cations, RC≡CAg2+ (R = Me and Ph) with allyliodide

Alkynylsilver cations, RCCAg2+ (where R = Me and Ph) have been prepared in the gas phase using multistage mass spectrometry experiments in a quadrupole ion trap mass spectrometer. Two methods were used: (i) electrospray ionisation (ESI) of a mixture of AgNO3 (in MeOH/H2O/acetic acid) and the alkyne carboxylic acid to yield the appropriate silver acetylide cations RCCAg2+, via a facile decarboxylation of the RCCCO2Ag2+ precursor; (ii) ESI of silver acetylides, RCCAg, which yields a cluster of the type, [(RCCAg)12Ag2Cl]+. Regardless of the method of preparation, these alkynylsilver cations, RCCAg2+, undergo ion-molecule reactions with allyliodide to yield the ionic products Ag 2I+ and [(RCCCH2CHCH2)Ag] +. The CID spectrum of [(PhCCCH2CHCH2)Ag] + was compared to that of an authentic sample of the silver adduct of 5-phenyl-1-penten-4-yne. Both ions fragment to yield Ag+ and the radical cation, PhCCCH2CHCH2+, confirming that C-C bond coupling has taken place in the gas phase. DFT calculations were carried out on these C-C bond coupling reactions for the system R = Me. The reaction is highly exothermic and involves the initial coordination of the allyliodide to both silver atoms, with the iodine coordinating to one atom and the alkene moiety coordinating to the other. The overall mechanism of C-C bond coupling involves oxidative addition of the allyliodide followed by reductive elimination of RCCCH2CHCH2, to ultimately yield two sets of reaction products: (i) Ag2I+ and RCCCH 2CHCH2; and (ii) [(RCCCH2CHCH 2)Ag]+ and AgI. The Royal Society of Chemistry 2013.

Core-satellite heterostruture of Fe3O4-Pd nanocomposite: Selective and magnetically recyclable catalyst for decarboxylative coupling reaction in aqueous media

Fe3O4-Pd nanocomposite having core-satellite heterostructure, prepared through the reaction of Pluronic polymer (P123, PEO19-PPO69-PEO19)-coated Fe3O 4 nanoparticle and Na2

One-pot three component synthesis of 5-allyl-1,2,3-triazoles using copper(i) acetylides

One-pot three-component reactions using copper(i) acetylide, azide, allyl iodide, and NaOH have been developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further transformed into a variety of 1,2,3-triazole-fused bi-/tricyclic scaffolds. This method offers the most efficient, convenient, and practical route towards useful polycyclic scaffolds in moderate to excellent yields.

Selective Alkynylallylation of the C?C σ Bond of Cyclopropenes

A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C?C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp2)-C(sp3) bond scission with conjunctive cross-couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram-scale products can be easily obtained by such a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations afford a rationale toward the formation of the products and indicate that the selective insertion of the double bond of cyclopropenes into the C-Pd bond of ambidentate Pd complex and the subsequent nonclassical β-C elimination promoted by 1,4-palladium migration are critical for the success of the reaction.

Nickel-Catalyzed Allylmethylation of Alkynes with Allylic Alcohols and AlMe3: Facile Access to Skipped Dienes and Trienes

We present herein an unprecedented allylative dicarbofunctionalization of alkynes with allylic alcohols. This simple catalytic procedure utilizes commercially available Ni(COD)2, triphenylphosphine, and inexpensive reagents, and delivers valuable skipped dienes and trienes with an all-carbon tetrasubstituted alkene unit in a highly stereoselective fashion. Preliminary mechanistic studies support the reaction pathway of allylnickelation followed by transmetalation in this dicarbofunctionalization of alkynes.

A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH 2 is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1,2,3-triazoles with high yields and good selectivity under mild reaction conditions.

Synthesis of aryl allyl alkynes via reaction with allyl amine and aryl alkynoic acids through decarboxylation

Allyl alkynoic esters were synthesized by the reaction of allyl amines and alkynoic acids via deaminative esterification. The reaction of allyl alkynoic esters with Pd(dba)2 and Xantphos in digylme at 110 °C for 12 h afforded the desired decarb

Catalytic Regio- and Enantioselective Proton Migration from Skipped Enynes to Allenes

Chiral allenes are highly valuable as versatile synthetic intermediates and core skeletons of various functional organic molecules. Despite marked recent advances, the straightforward catalytic enantioselective synthesis of hydrocarbon allenes from readil

Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement

The gold(I)-catalyzed reaction of bromoalkynes with allylsilanes gives 1,4-enynes in a formal cross-coupling reaction. Mechanistic studies revealed the involvement of gold(I) vinylidenes or vinylidenephenonium gold(I) cations depending on the substituent on the bromoalkyne. In the case of bromo arylalkynes, the vinylidenephenonium gold(I) cations lead to 1,4-enynes via a 1,2-aryl rearrangement. The same reactivity has been observed in the presence of InBr3