159527-72-7

Basic information

• Product Name: Ethanone, 1-[4-(1,2-propadienyl)phenyl]- (9CI)
• Synonyms: Ethanone, 1-[4-(1,2-propadienyl)phenyl]- (9CI)
• CAS NO: 159527-72-7
• Molecular Formula: C₁₁H₁₀O
• Molecular Weight: 158.1965
• Product Categories: ACETYLGROUP
• Mol File: 159527-72-7.mol

Chemical Properties

• Boiling Point: 301.0±12.0 °C(Predicted)
• Appearance: /
• Density: 0.976±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Ethanone, 1-[4-(1,2-propadienyl)phenyl]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[4-(1,2-propadienyl)phenyl]- (9CI)(159527-72-7)
• EPA Substance Registry System: Ethanone, 1-[4-(1,2-propadienyl)phenyl]- (9CI)(159527-72-7)

Safety Data

• Hazardous Substances Data: 159527-72-7(Hazardous Substances Data)

Upstream product

• 99-90-1 para-bromoacetophenone 
• 50-00-0 formaldehyd 
• 1198086-87-1 3-(4-acetylphenyl)propiolic acid 
• 42472-69-5 4-ethynylacetophenone 
• 108-18-9 diisopropylamine 
• 13329-40-3 4-Iodoacetophenone 
• 53915-69-8 allenyltributylstannane 
• 106-96-7 propargyl bromide 
• 69497-83-2 4-acetylphenyl mesylate 

Downstream Products

• 1039513-47-7 (E)-1,1'-(4,4'-(5-oxocyclopent-3-ene-3-yl-1-ylidene)bis(methylene)bis(4,1-phenylene))diethanone 
• 1039513-43-3 (E)-1,1'-(4,4'-(4-oxocyclopent-2-ene-2-yl-1-ylidene)bis(methylene)bis(4,1-phenylene))diethanone 
• 502431-19-8 CH₃COC₆H₄CHC(Si(CH₃)3)(CH₂Sn(C₄H₉)3) 

Relevant articles and documents

The Stille coupling reaction of aryl triflates with n-tributylallenyl stannane: a general route to arylallenes.

The palladium-copper co-catalyzed cross-coupling reaction of n-tributylallenyl stannane 1 with aryl triflates provides an efficient route to the corresponding aryl allenes.

1,2-Bis(diphenylphosphino)carborane as a dual mode ligand for both the Sonogashira coupling and hydride-transfer steps in palladium-catalyzed one-pot synthesis of allenes from aryl iodides

One-pot allene synthesis from aryl iodides 1 and propargyldicyclohexylamine 2 proceeded in the presence of Pd2(dba)3·CHCl 3 catalyst (2.5 mol %), 1,2-bis(diphenylphosphino)carborane 5 (10 mol %), Cul (15 mol %), and Et3N (150 mol %) to give the corresponding allenes 4 in good to high yields. Electron-deficient bidentate phosphines, such as 1,2-bis(diphenylphosphino)carborane 5 and (C6F5) 2PC2H4P(C6F5) 2, play the role of a dual mode ligand for both the Sonogashira coupling and hydride-transfer reactions.

Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO2

The photoredox-catalyzed α-aminoalkylcarboxylation of aryl allenes with CO2 and N,N-dimethylanilines is reported for the first time (26 examples, up to 96% yield). In the case of electron-deficient allenes, good regioselectivity was observed (up to 94:6), exclusively generating kinetic products over thermodynamic products. This protocol is a novel synthetic method for highly functionalized β,γ-unsaturated γ-aminobutyric esters.

Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids

Synthesis of terminal allenes via a copper-catalyzed decarboxylative coupling reaction was developed. Aryl alkynyl carboxylic acid, paraformaldehyde, and dicyclohexylamine were reacted with CuI (20 mol %) in diglyme at 100°C for 2 h to produce the terminal allene in moderate to good yields. The method showed good functional group tolerance.

Effect of varying the anionic component of a copper(I) catalyst on homologation of arylacetylenes to allenes by the Mannich reaction

The effect of varying the anionic component of a copper(I) catalyst in the homologation of terminal arylacetylenes to allenes by the Mannich reaction was investigated. Varying amounts of allenes, Mannich bases and dimers were obtained depending on the nature of the anionic component of the copper catalyst. On the other hand, Eglinton-Glaser dimerizations were achieved in high yields with 0.5 equiv. of triethylamine. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of ene-allenes via palladium-catalyzed hydride-transfer reaction of propargylic amines under mild conditions

The palladium-catalyzed allene transformation reaction from propargylic amines proceeded in the presence of Pd2(dba)3· CHCl3 (5 mol %) and (C6F5)2PC 2H4P(C6

Highly chemoselective coupling of allenylstannanes with organic iodides promoted by Pd(PPh3)4/LiCl: An efficient method for the synthesis of substituted allenes

An efficient method for the preparation of various monosubstituted arylallenes, disubstituted allenes and alkenylallenes via palladium-catalyzed coupling of allenylstannanes with aryl iodides or alkenyl iodides is described. The coupling reaction was carr

Highly efficient catalytic synthesis of substituted allenes using indium

Versatile, convenient, mild: Allenylindium intermediates generated from the reaction of indium with propargyl bromides were employed as effective coupling partners in Pd-catalyzed cross-coupling reactions with a variety of electrophiles to produce allenes, polyallenes, and unsymmetrical bis(allenes) in excellent yields with complete regioselectivity and chemoselectivity (see scheme for one example).