10271-65-5

Basic information

• Product Name: 1-(o-biphenylyl)-2-phenylethyne
• Synonyms: 1-(o-biphenylyl)-2-phenylethyne;2-(Phenylethynyl)-1,1-biphenyl
• CAS NO: 10271-65-5
• Molecular Formula: C₂₀H₁₄
• Molecular Weight: 254.32516
• EINECS: -0
• Mol File: 10271-65-5.mol
• Article Data: 33

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(o-biphenylyl)-2-phenylethyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(o-biphenylyl)-2-phenylethyne(10271-65-5)
• EPA Substance Registry System: 1-(o-biphenylyl)-2-phenylethyne(10271-65-5)

Safety Data

• Hazardous Substances Data: 10271-65-5(Hazardous Substances Data)

Usage

Description

1-(o-biphenylyl)-2-phenylethyne, also known as 1-phenyl-2-(2-phenylethynyl)benzene, is a chemical compound that features a biphenyl group connected to a phenylethyne group. This unique molecular structure endows it with diverse chemical reactivity and potential for various applications in organic synthesis, research, pharmaceuticals, and materials science.

Uses

Used in Organic Synthesis:
1-(o-biphenylyl)-2-phenylethyne is used as a building block for the production of other organic compounds, leveraging its distinctive molecular structure to facilitate the creation of complex molecules.
Used in Research:
In the field of research, 1-(o-biphenylyl)-2-phenylethyne serves as a starting material for the synthesis of intricate molecular structures, contributing to the advancement of chemical knowledge and innovation.
Used in Pharmaceutical Industry:
1-(o-biphenylyl)-2-phenylethyne is utilized as a precursor in the development of pharmaceuticals, potentially contributing to the discovery of new drugs due to its unique chemical properties and reactivity.
Used in Materials Science:
Within materials science, 1-(o-biphenylyl)-2-phenylethyne is explored for its potential to enhance or create new materials with specific properties, such as improved conductivity or structural integrity.
1-(o-biphenylyl)-2-phenylethyne's potential biological and pharmacological properties are also under investigation, which could lead to further applications in the medical and healthcare sectors.

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 2113-51-1 2-iodobiphenyl 
• 6738-06-3 phenylethynylmagnesium bromide 
• 17763-65-4 biphenyl-2-yl trifluoromethanesulfonate 
• 264912-30-3 1-(o-biphenylyl)-1,2-dibromo-2-phenylethane 
• 591-51-5 phenyllithium 
• 42168-23-0 2-(phenylethynyl)phenyllithium 
• 55365-18-9 biphenyl-2-yl-lithium 
• 4440-01-1 lithium phenylacetylide 
• 63383-46-0 1-(trimethylsiloxy)-1,3-butadiene 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 2052-07-5 2-Bromobiphenyl 
• 536-74-3 phenylacetylene 
• 34662-94-7 1-phenyl-2-(2'-biphenylyl)ethylene 

Downstream Products

• 1836-87-9 9-Benzylidene-9H-fluorene 
• 844-20-2 9-phenylphenanthrene 
• 1420771-05-6 phenyl(10-phenylphenanthren-9-yl)sulfane 
• 60300-72-3 4,5-diphenylacephenanthrylene 
• 1420771-22-7 methyl(10-phenylphenanthren-9-yl)sulfane 
• 68622-84-4 (Z)-2-styryl-1,1'-biphenyl 

Relevant articles and documents

The first example of formation of the benzyne intermediate from the reactions of selenonium salts with phenyllithium

The reaction of diphenyl(phenylethynyl)selenonium salt 1a with 1.0 equiv. of phenyllithium afforded 1,4-diphenylbutadiyne 5 and 1-(o- biphenylyl)-2-phenylethyne 7 in 25% and 15% yields, respectively. The latter product 7 was formed via the benzyne intermediate.

Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids

Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis is presented. The carboxylic acid is activated in situ by the formation of a mixed anhydride and further decarbonylates using the Pd(OAc)2/Xantphos system to provide an aryl-Pd intermediate, which is intercepted by alkynes to access the traditional Pd(0)/(II) cycle using carboxylic acids as ubiquitous and orthogonal electrophilic cross-coupling partners. The methodology efficiently constructs new C(sp2)-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.

Cobalt(I)-catalyzed neutral Diels-Alder reactions of oxygen-functionalized acyclic 1,3-dienes with alkynes

The cobalt-catalyzed Diels-Alder reaction of alkoxy-substituted 1,3-butadienes with terminal and internal alkynes is described. While the reaction of 1-alkoxy derivatives gave the aromatic hydrocarbons upon elimination of alcohol from the alkoxy-substituted dihydroaromatic intermediates, the reactions with 2-alkoxy derivatives generated stable dihydroaromatic enol ethers in good to excellent chemical yields and good to high regioselectivities for unsymmetrical starting materials. The enol ethers can be easily hydrolysed to the corresponding β,γ-unsaturated ketones in a one pot reaction sequence or used in cyclopropanation or other subsequent chemical transformations.

Metal-Free Synthesis of Selenodihydronaphthalenes by Selenoxide-Mediated Electrophilic Cyclization of Alkynes

A transition-metal-free, selenium mediated electrophilic cyclization reaction was realized through a one-pot procedure between simple alkynes and triflic anhydride-activated selenoxides to give selenium containing dihydronaphthalene products. This method gave good to very high yields for all products, including selenium-substituted phenanthrene, dihydroquinoline, 2H-chromene, and coumarin, which can be further transformed to other functionalized compounds.

Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids

A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.