4614-01-1

Usage

Type of compound

Indene, a bicyclic hydrocarbon with a benzene ring fused to a cyclopentadiene ring

Structure

Three phenyl groups attached to the indene ring

Common uses

a. Organic synthesis
b. Production of organic electronic materials
c. Intermediate in the synthesis of pharmaceuticals and agrochemicals

Unique properties

a. Aromatic properties
b. Valuable building block for creating a variety of chemical products

Potential applications

a. Materials science
b. Pharmaceuticals
c. Agrochemicals

Upstream product

• 27674-41-5 1,1,2,2-tetraphenyl-2-propen-1-ol 
• 1674-18-6 tetraphenylallene 
• 876480-32-9 (+/-)-3-Hydroxy-1.1.3-triphenyl-indan 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 536-74-3 phenylacetylene 
• 109-99-9 tetrahydrofuran 
• 108-86-1 bromobenzene 
• 4467-88-3 1,3-diphenylindene 
• 1961-96-2 1-phenyl-1H-indene 
• 591-50-4 iodobenzene 
• 95-13-6 1-indene 
• 55010-17-8 3,3-diphenyl-indan-1-one 
• 67-56-1 methanol 

Downstream Products

• 38274-35-0 1,2,3-triphenylindene 
• 73010-42-1 1,1,3-Triphenylindane 
• 861523-65-1 (2-benzoyl-phenyl)-diphenyl-acetic acid 
• 42523-79-5 1,3,3-Triphenyl-indan-2-ol 
• 77387-99-6 2-Brom-1,1,3-triphenylinden 
• 31366-67-3 1,2,3-triphenylindan 
• 56849-86-6 methyl-(1,2,3-triphenyl-inden-1-yl)-ether 
• 40112-66-1 1,1,3-triphenyl-2-indanone 

Relevant academic research and scientific papers

Microwave-Assisted Condensation of Benzylic Alcohols and Alkynes Promoted by Zinc Halides: Concise Access to Alkenyl Halides

A simple Lewis acid-mediated route for the synthesis of alkenyl halides are described under microwave-assisted conditions. The reaction proceeds through the condensation between secondary alcohols and terminal acetylenes and regioselective hydrohalogenati

Rhodium-Catalyzed Expeditious Synthesis of Indenes from Propargyl Alcohols and Organoboronic Acids by Selective 1,4-Rhodium Migration over β-Oxygen Elimination

An expeditious synthetic route to 1,1-disubstituted indenes from propargyl alcohols and organoboronic acids was developed under rhodium catalysis, and selective 1,4-rhodium migration over β-oxygen elimination was involved as the key step. DPEphos was foun

Regiocontrolled hydroarylation of (trifluoromethyl)acetylenes in superacids: Synthesis of CF3-substituted 1,1-diarylethenes

The reactions between aryl(trifluoromethyl)-substituted alkynes and arenes in triflic and fluorosulfonic acids were investigated. These reactions proceeded 100 % regioselectively to give 1,1-diaryl-2-trifluoromethylethenes in high yields. Depending on the

Reactions of arylacetylenic compounds with arenes in the presence of aluminum halides

Conjugated arylacetylenic ketones and aldehydes, propargyl-type alcohols, and arylacetylenes reacted with arenes in the presence of AlBr3 or AlCl3 as catalyst to give substituted indenes. 3-Arylpropynoic acids under analogous conditi

Palladium-catalyzed arylation of cyclopentadienes

Cyclopentadiene and metallocenes, typically zirconocene dichloride, are suitable substrates for multiple arylations with aryl bromides in palladium-catalyzed reactions. Thus, various aryl bromides bearing either an electron-donating or an electron-withdrawing substituent can react with these substrates to afford the corresponding 1,2,3,4,5-pentaaryl-1,3-cyclopentadienes in a single preparative step. Derivatives of cyclopentadiene, including di- and trisubstituted cyclopentadienes, and indene are arylated in a similar fashion.

1,n-Radical ions. Photosensitized (electron transfer) and electrochemical oxidation of 1,1,2,2-tetraphenylcyclopropane

The photosensitized (electron transfer) and electrochemical oxidation of 1,1,2,2-tetraphenylcyclopropane (1) have been studied.The products obtained from the photosensitized (electron transfer) study are 1,1,3,3-tetraphenylpropene (2), 1,3,3-triphenylindene (3), tetraphenylallene (4), and 3-methoxy-1,1,3,3-tetraphenylpropene (8).The product ratios are dramatically dependent upon the reaction conditions, particularly sensitizer (aromatic nitriles, tetracyanoethylene, chloranil, and 2,3-dichloro-5,6-dicyanobenzoquinone were used), and solvent.The variation in product ratios are attributed to variations in the redox behaviour of the sensitizer radical anion and upon the basicity and nucleophilicity of the medium.The products in the electrochemical study are 3,4, and 8.Common intermediates have been identified and a mechanism for the formation of product is proposed.

A CONVENIENT SYNTHESIS OF 2-PHENYLINDENE

A benzene solution of phenylacetic acid when passed over alumina at 420 deg C gave 2-phenylindene.

The SRN1 Photoarylation of Indenyl Anions

Irradiation of Me2SO solutions of indenyl anion and its phenylated analogues in the presence of bromobenzene produces the higher phenylated indenes.Thus indenyl anion (1b) yields 3-phenylindene (3a), 1-phenylindenyl anion (3b) yields 1,3- and 1,1-diphenylindene, 2-phenylindenyl anion (2b) produces 2,3-diphenylindene, 1,3-diphenylindenyl anion (6b) produces 1,1,3- and 1,2,3-triphenylindene, and 1,2-diphenylindenyl anion (5b) produces 1,2,3-triphenylindene (8).In liquid ammonia and tetrahydrofuran more complex reaction pathways are observed.The regiochemistry of phenylation is attributed to radical attack at the most basic site, in accord with a previously published model.