122778-92-1

Basic information

• Product Name: Phenol, 4-methyl-2-(phenylethynyl)-
• CAS NO: 122778-92-1
• Molecular Formula: C15H12O
• Molecular Weight: 208.26
• Mol File: 122778-92-1.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 4-methyl-2-(phenylethynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 4-methyl-2-(phenylethynyl)-(122778-92-1)
• EPA Substance Registry System: Phenol, 4-methyl-2-(phenylethynyl)-(122778-92-1)

Safety Data

• Hazardous Substances Data: 122778-92-1(Hazardous Substances Data)

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 7577-76-6 4-acetoxy-4-methyl-2,5-cyclohexanedienone 
• 16188-57-1 2-iodo-4-methylphenol 
• 536-74-3 phenylacetylene 
• 1620889-19-1 C₁₇H₁₆O₂ 
• 122778-73-8 3-(2-Hydroxy-5-methylphenyl)-2-phenylcyclopropenon 

Downstream Products

• 25871-52-7 5-methyl-2-phenylbenzofuran 
• 1352954-88-1 C₂₂H₁₇NO₄ 
• 1309774-48-8 1-allyl-5-chloro-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-47-7 1-allyl-5-fluoro-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-46-6 1-allyl-6-methoxy-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-40-0 1-allyl-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-43-3 5-bromo-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-41-1 5-fluoro-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-38-6 1-methyl-3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 
• 1309774-37-5 3-(5-methyl-2-phenylbenzofuran-4-yl)-1H-indole 

Relevant articles and documents

Metal-Free Radical Annulation of Oxygen-Containing 1,7-Enynes: Configuration-Selective Synthesis of (E)-3-((Arylsulfonyl)methyl)-4-Substituted Arylidenechromene Derivatives

A novel strategy for the synthesis of (E)-3-((arylsulfonyl)methyl)-4-substituted benzylidenechromene derivatives via a metal-free radical annulation reaction of oxygen-containing 1,7-enynes with thiosulfonates has been developed. The reaction shows broad substrate scope, wide functional group tolerance, and moderate to excellent yields. Moreover, thiosulfonates were well driven to achieve the bifunctionalization reaction of oxo-1,7-enynes which derived from aliphatic alkynes. In addition, the (E)-configuration of the products was highly controlled by the structure of 1,7-enyne.

A Facile Construction of Bisheterocyclic Methane Scaffolds through Palladium-Catalyzed Domino Cyclization

A convenient palladium-catalyzed domino cyclization reaction for the construction of bis(benzofuranyl)methane scaffolds bearing an all-carbon quaternary center has been described. In the cascade process, one C(sp2)—O bond, two C(sp2)—C(sp3) bonds as well as two benzofuran rings are formed in a single synthetic sequence. The approach shows wide scope of substrates and good functional-group tolerance. Moreover, this methodology is successfully extended to the synthesis of benzofuranyl methyl chromane derivatives.

Indium(III)-Catalyzed Synthesis of Benzo[ b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights

Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group.

Copper-Iodide- and Diorganyl-Diselenide-Promoted Cyclization of 2-Alkynylphenols: Alternative Approach to 3-Organoselanylbenzo[b]furans

This paper describes an alternative method for the synthesis of 3-organoselanylbenzo[b]furans through the intramolecular cyclization of 2-alkynylphenols promoted by copper iodide and diorganyl diselenides. The cyclization reactions were carried out at roo

A Palladium-Catalyzed Domino Approach to 2,3-Disubstituted Benzofurans via an Intermolecular Carbopalladation/C(sp3)?H Functionalization/Isomerization Sequence

A palladium-catalyzed domino strategy has been developed for the synthesis of 2,3-disubstituted benzofuran derivatives. This cascade reaction sequence involves intermolecular carbopalladation and C(sp3)?H functionalization followed by isomerization. (Figure presented.).

Highly efficient heterogeneous synthesis of benzofurans under aqueous condition

Highly efficient organic reactions in water are important for designing environmental-friendly and low cost synthetic processes. Herein, we demonstrate an intermediate-in-water strategy for the heterogeneous synthesis of benzofurans in aqueous media. The cyclization reaction of 2-(phenylethynyl)phenol to 2-phenylbenzofuran cannot proceed in pure water. However, this reaction can be efficiently promoted by the formation of sparingly soluble intermediate in the presence of alkaline. Quantitative conversion of a variety of substrates to benzofuran derivatives has been achieved in the absence of noble metal catalyst. Other remarkable features including easy-isolation and purification of product, along with wide range of functional group tolerance render the methodology promising in the realm of green-synthesis.

Tandem gold-catalyzed hydrosilyloxylation-aldol and -Mannich reaction with alkynylaryloxysilanols in 6-exo mode

The tandem gold-catalyzed hydrosilyloxylation-aldol and hydrosilyloxylation-Mannich reactions were developed through the formation of an enol silyl ether catalytically generated in situ from alkynylaryloxysilanols in the 6-exo mode in one reaction vessel. Copyright

Potassium tert-butoxide promoted annulation of 2-alkynylphenyl propargyl ethers: Selective synthesis of benzofuran and 12H-benzoannulene derivatives

We present here our results on potassium tert-butoxide promoted annulation reactions of 2-alkynylphenyl propargyl ethers to give two different types of heterocycles: 3-benzyl-2-alkynylbenzofurans and 12H-benzoannulenbenzo[b]furans. A series of functionalized 2-alkynylphenyl propargyl ethers were efficiently cyclized by potassium tert-butoxide to the corresponding products. The optimized reaction conditions tolerated a large variety of functional groups, including electron-rich, electron-poor, and N-heterocyclic substrates. Selective product formation was obtained by controlling the solvent and temperature. When THF was used at room temperature, 3-benzyl-2-alkynylbenzofuran derivatives were exclusively obtained, while the use of DMF at 60 C gave selectively 12H-benzoannulen[b]benzofurans.

Gold-catalyzed cyclizations of (o-alkynyl)phenoxyacrylates with external nucleophiles: Regio-and stereoselective synthesis of functionalized benzo[b]oxepines

A catalytic approach to benzo[b]oxepines with high stereoselectivity by Au-catalyzed cyclization of (o-alkynyl)phenoxyacrylates with various nucleophiles under mild reaction conditions has been developed. Notably, the use of vinyl ether instead of alcohol could afford the same benzoxepines. The reaction may proceed by Au-catalyzed oligomerization of vinyl ether to release the alcohol, which then reacts with (o-alkynyl)phenoxyacrylates to furnish the benzoxepines.

Cationic palladium(II)-catalyzed synthesis of 2-substituted 3-hydroxymethylbenzo[b]furans

A tandem reaction involving an intramolecular oxypalladation of an alkyne and an addition to the carbonyl group to quench the carbon-palladium bond to complete the catalytic cycle was developed. The reaction was catalyzed with the cationic palladium(II) species without the necessity of a redox system. Georg Thieme Verlag Stuttgart · New York.