22256-19-5

Usage

Physical state

Colorless liquid

Aroma

Sweet, floral

Common uses

Production of pharmaceuticals, fragrances, and as a precursor for the synthesis of other organic compounds

Health properties

Anti-inflammatory and analgesic

Safety precautions

Can irritate skin and eyes, harmful if ingested or inhaled in large quantities

Upstream product

• 108-86-1 bromobenzene 
• 95-13-6 1-indene 
• 5324-00-5 2,3-diphenyl-1H-indene 
• 52095-44-0 (E)-2-styrylbenzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 100-42-5 styrene 
• 1323308-07-1 (E)-phenyl(2-styrylphenyl)methanol 
• 1801-42-9 2,3-diphenyl-1H-inden-1-one 
• 18949-22-9 1,1-dimethyl-2,3-diphenyl-1H-indene 
• 1105026-33-2 2-methyl-3,4,4-triphenyl-2-butanol 
• 13740-67-5 2,2-diphenyl-1-indanone 
• 18636-54-9 1,2-diphenyl-1H-indene 
• 78579-95-0 lithium 4a,5-dihydro-10-phenyl-2H-dibenzocyclohepten-2-ide 

Relevant academic research and scientific papers

Asymmetric Reductive Dicarbofunctionalization of Alkenes via Nickel Catalysis

Alkenes are an appealing functional group that can be transformed into a variety of structures. Transition-metal catalyzed dicarbofunctionalization of alkenes can efficiently afford products with complex substitution patterns from simple substrates. Under reductive conditions, this transformation can be achieved while avoiding stoichiometric organometallic reagents. Asymmetric difunctionalization of alkenes has been underdeveloped, in spite of its potential synthetic utility. Herein, we present a summary of our efforts to control enantioselectivity for alkene diarylation with a nickel catalyst. This reaction is useful for preparing triarylethanes. The selectivity is enhanced by an N -oxyl radical additive.

Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes

A nickel-catalyzed asymmetric diarylation reaction of vinylarenes enables the preparation of chiral α,α,β-triarylated ethane scaffolds, which exist in a number of biologically active molecules. The use of reducing conditions with aryl bromides as coupling partners obviates the need for stoichiometric organometallic reagents and tolerates a broad range of functional groups. The application of an N-oxyl radical as a ligand to a nickel catalyst represents a novel approach to facilitate nickel-catalyzed cross-coupling reactions.

Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of (Z)- and (E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives

Starting from bromo/iodobenzaldehyde derivatives, the corresponding (Z)- and (E)-(2-stilbenyl)methanols could be prepared in 2-5 steps via Pd-catalyzed cross-coupling reactions (Sonogashira and Heck reactions) followed by aryllithium/aryl Grignard addition. For the (E)-stilbenes, subsequent acid-mediated cyclization using p-TsOH immobilized on silica (PTS-Si) at low temperatures furnished the 2,3-trans-1-indanols with complete stereocontrol at the C2-C3. Further oxidization of the alcohol provided the indanones, which are structurally related to the natural product paucifloral F. At higher temperatures, 1,2- and 2,3-disubstituted indenes could be selectively prepared in good to excellent yields. On the other hand, the (Z)-stilbenes, under similar conditions (PTS-Si), did not give the indanols; only the 1,2-disubstituted indenes could be obtained. To gain further insights into the stereochemistry at C2-C3 for the (Z)-stilbenes, hydride or azide was employed as a nucleophile; the corresponding indane products were obtained with the cis stereochemistry at the C2-C3. Thus, the (Z)- or (E)-olefin geometry of the substrate directed the stereoselective indanyl cyclization to furnish the cis or trans at the C2-C3 ring junction, respectively, while reaction conditions controlled the selectivity of the product types.

Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids

The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diaste

Synthesis of substituted 2-arylindanes from e -(2-stilbenyl)methanols via lewis acid-mediated cyclization and nucleophililc transfer from trialkylsilyl reagents

A preparative method for the synthesis of functionalized 2-arylindanes has been developed via the Lewis acid-mediated ring closure of stilbenyl methanols followed by nucleophilic transfer from trialkylsilyl reagents. The reactions gave the corresponding p

Modern Friedel-Crafts chemistry. Part-29. Cyclialkylation of some triphenylated propane, butane and pentane substrates to diphenylated indans under Friedel-Crafts conditions

Reactions under Friedel-Crafts cyclialkylation conditions produced : isomeric 1,2-diphenylindans from 1,2,3-triphenyl-(1- or 2-)propanol and 1-chloro-2,3,3-triphenylpropane, trans-2-benzyl-1-phenylindan from 2-benzyl-1,3-diphenyl-2-propanol, isomeric 1-me

Synthesis and nuclear magnetic resonance spectroscopy of indane structures: indanes mono- and disubstituted in the pentagonal ring

Indanes monosubstituted and 1,2- and 1,3-disubstituted in the pentagonal ring were synthesized, and configurations were assigned to the 1,2-disubstituted compounds by means of nuclear magnetic resonance spectroscopy.Key words: mono- and disubstituted indanes, conformation, configuration, 1H and 13C NMR, synthesis.

Electrochemical Reduction of Activated Carbon-Carbon Double Bonds. Part 2. Mechanism and Stereochemistry of the Reduction of Self-protonating Indenes

The reduction at a mercury electrode in dimethylformamide of five variously substituted indenes bearing at least one (acidic) hydrogen at C(1) was carried out, under self-protonation conditions and in the presence of phenol as a proton donor.Reduction occ

Electrochemical Reduction of Activated Carbon-Carbon Double Bonds. 1. Mechanism and Stereochemistry of the Reduction of Phenyl-Substituted Indenes

The reduction at a Hg electrode in DMF of some phenyl-substituted indenes was carried out, with the aim of finding out possible relationships between stereochemistry and mechanism of the reaction.The two-electron two-proton reduction occured exclusively a

Vinyl-to-Benzyl Isomerization and Electrocyclizations in Lithio Derivatives of o-Tolylstilbenes

(Z)-2-(2-Methylphenyl)-1,2-diphenylvinyllithium (1) isomerizes in THF solution to give 1--1,2-diphenylethene (2).Although 2 cannot be observed directly in this case, its intermediacy becomes evident from the independent preparation