2444-68-0

Usage

Uses

Used in Organic Synthesis:
9-VINYLANTHRACENE is used as a key compound for [application reason] in the field of organic synthesis. Its unique chemical properties allow it to participate in a wide range of reactions, making it a valuable asset for the creation of new molecules and materials.
Used in Chemical Research:
In the realm of chemical research, 9-VINYLANTHRACENE is used as a research tool for [application reason]. Its distinctive properties enable scientists to study various aspects of chemical reactions and mechanisms, contributing to the advancement of knowledge in the field.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 9-VINYLANTHRACENE is used as an intermediate for [application reason]. Its role in the synthesis of various drugs and medications makes it an essential component in the development of new treatments and therapies.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 9-VINYLANTHRACENE is used as a colorant for [application reason]. Its yellow to green crystalline solid form provides a unique color profile that can be utilized in the creation of various dyes and pigments for different applications.
Used in Polymer Science:
9-VINYLANTHRACENE is also used as a monomer in the field of polymer science for [application reason]. Its ability to form polymers with specific properties makes it a valuable component in the development of new materials with tailored characteristics for various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 4035, 1991 DOI: 10.1021/jo00012a043Synthesis, p. 319, 1981

Purification Methods

Purify it by vacuum sublimation. It has also been purified by chromatography on silica gel with cyclohexane as eluent, and recrystallised from EtOH [Werst et al. J Am Chem Soc 109 32 1987]. [Beilstein 5 IV 2415.]

InChI:InChI=1/C16H12/c1-2-14-15-9-5-3-7-12(15)11-13-8-4-6-10-16(13)14/h2-11H,1H2

Upstream product

• 3990-97-4 tert-Butyl β-(9-anthryl)perpropanoate 
• 78612-92-7 9-Vinyl-9,10-dihydro-anthracen-9-ol 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 642-31-9 9-anthracene aldehyde 
• 18424-76-5 dimethyl malonate sodium salt 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 74928-67-9 9-(1-hydroxyethyl)anthracene 
• 1564-64-3 9-Bromoanthracene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 74-88-4 methyl iodide 
• 96689-10-0 9-Vinyl-anthracene; compound with tetranitro-methane 
• 593-60-2 Vinyl bromide 
• 90-44-8 anthracen-9(10H)-one 
• 1112-54-5 vinyltriethylsilane 

Downstream Products

• 98-82-8 Isopropylbenzene 
• 61695-73-6 1-(9-anthryl)-ethylene oxide 
• 84332-58-1 ω-(anthracene-9-yl)ethanal 
• 54060-73-0 2-(9-anthryl)ethanol 
• 7512-20-1 (-)-(S)-1-Anthracen-9-ylethanol 
• 7512-20-1 (R)-1-(9-Anthryl)ethanol 
• 84-65-1 9,10-phenanthrenequinone 
• 642-31-9 9-anthracene aldehyde 
• 203578-97-6 (S)-2-hydroxy-2-(9-anthracenyl)ethyl mesitylene sulfonate 
• 42196-97-4 9-trans-styryl-anthracene 
• 784-04-3 9-acetylanthracene 
• 1646848-89-6 2-(anthracen-9-yl)-N-benzyl-N-methylethanamine 

Relevant academic research and scientific papers

Synthesis and Reaction of Anthracene-Containing Polypropylene: A Promising Strategy for Facile, Efficient Functionalization of Isotactic Polypropylene

A novel anthracene-containing isotactic polypropylene (An-iPP) with high molecular weight (>10 × 104) and satisfying incorporation (5.7 mol %) was synthesized via direct copolymerization of propylene and 9-hexenylanthracene. The pendent anthryl group of the resulting An-iPP is quite active, and this provides a facile and efficient avenue to synthesize various functional iPPs. As a typical and important example, maleic anhydride (MA) functionalized polypropylene, was successfully prepared in a highly efficient, catalyst-free, byproduct-free, and controllable way via mild Diels-Alder (D-A) reaction between pendent anthryl groups and MA. More importantly, the D-A functionalization process did not sacrifice the original properties of the An-iPP, as no unfavorable degradation and cross-linking were detected in DSC and GPC analyses. Besides MA, several other dienophiles could also be conveniently used as functional reagents to prepare various functionalized iPPs with distinct properties. The unique fluorescent property of An-iPP was studied and could be used for functionalization process monitoring.

Functionalization of Alkenyl C-H Bonds with D 2 O via Pd(0)/Carboxylic Acid Catalysis

We report herein a simple catalytic method for the extensive labeling of alkenyl C-H bonds through the combination of a palladium(0) complex and a carboxylic acid in the presence of deuterium oxide. The reaction can be applied to a variety of terminal alkenes and the best results are obtained with aryl-substituted examples. This method represents a convenient approach for the preparation of extensively labeled chemicals from the cheapest and safest source of deuterium.

Copper-Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes

A catalytic defluorinative hydroarylation of alkenes with polyfluoroarenes in the presence of dppbz-ligated Cu catalyst and silanes was developed. This method provides a straightforward and alternative avenue to synthetic important polyfluorinated arenes with readily available and bench-stable alkenes as latent nucleophiles, and therefore avoids conventional reliance on stoichiometric quantities of organometallic reagents. This reaction proceeds under very mild conditions and exhibits good functional group compatibility and high level of regioselectivity. The synthetic potential of this method was further demonstrated by a gram-scale synthesis, and an array of experimental studies were also carried out to elaborate the probable mechanism.

Photoinduced, copper-catalyzed three components cyanofluoroalkylation of alkenes with fluoroalkyl iodides as fluoroalkylation reagents

In the past few years, Ru and Ir catalyzed photoredox radical coupling reactions have been widely applied in organic synthesis. In contrast, the applications of Cu catalysts in photoredox organic transformations were limited. We here report the first example of photoinduced, Cu-catalyzed three component cyanofluoroalkylation of alkenes by directly using fluoroalkyl iodides as fluoroalkylation reagents.

Hantzsch Ester as a Photosensitizer for the Visible-Light-Induced Debromination of Vicinal Dibromo Compounds

The debromination of vicinal dibromo compounds to generate alkenes usually requires harsh reaction conditions and the addition of catalysts. Just recently the visible-light-induced debromination of vicinal dibromo compounds emerged as a possible alternative to commonly used methods, but the substrate scope of this reaction is limited and a photocatalyst is necessary for the successful conversion of the starting compounds. A catalyst-free visible-light-induced debromination of vicinal dibromo compounds with a base-activated Hantzsch ester as photosensitizer is reported. The method has a wide substrate scope and a broad functional-group compatibility.

Synthesis and photochemical transformations of a few olefin-appended 11,12-dibenzoyldibenzobarrelenes

Several olefin-appended dibenzobarrelenes have been synthesised by Diels-Alder reaction between 9-alkenylanthracenes and dibenzoylacetylene under carefully controlled conditions and their photochemistry was examined. Olefin appendages acted as efficient quenchers of the triplet state of these barrelenes.

Catalytic wittig reactions of semi- and nonstabilized ylides enabled by ylide tuning

The first examples of catalytic Wittig reactions with semistabilized and nonstabilized ylides are reported. These reactions were enabled by utilization of a masked base, sodium tert-butyl carbonate, and/or ylide tuning. The acidity of the ylide-forming proton was tuned by varying the electron density at the phosphorus center in the precatalyst, thus facilitating the use of relatively mild bases. Steric modification of the precatalyst structure resulted in significant enhancement of E selectivity up to >95:5, E/Z. Time for a tune up: Catalytic Wittig reactions with semi- and nonstabilized ylides were enabled by use of a masked base (NaOCO2tBu) and/or ylide tuning. The acidity of the ylide-forming proton was tuned by varying the electron density at the P center in the precatalyst, thus facilitating the use of relatively mild bases. Steric modification of the precatalyst structure resulted in significant enhancement of E selectivity.

METHODS FOR PHOSPHINE OXIDE REDUCTION IN CATALYTIC WITTIG REACTIONS

A method for increasing the rate of phosphine oxide reduction, preferably during a Wittig reaction comprising use of an acid additive is provided. A room temperature catalytic Wittig reaction (CWR) the rate of reduction of the phosphine oxide is increased due to the addition of the acid additive is described. Furthermore, the extension of the CWR to semi-stabilized and non-stabilized ylides has been accomplished by utilization of a masked base and/or ylide-tuning.

Evaluating the use of chiral anthracene templates to access pyroglutamic acids

An approach for the asymmetric synthesis of pyroglutamic acid derivatives is described based on an anthracene chiral auxiliary. The introduction of a furan ring as a masked carboxylic acid moiety proceeded with excellent levels of diastereo-selectivity, followed by conversion into a carboxylate ester. The ensuing retro-Diels-Alder procedure using flash vacuum pyrolysis (FVP) followed by reduction gave pyroglutamate esters in good yield but poor enantioselectivity, the latter of which was found to be dependant on the electronic nature of the N-protecting group.

Removal, recovery, and recycling of triarylphosphonium-supported tin reagents for various organic transformations

Phosphonium-supported tin reagents and catalysts were prepared and were shown to be effective in Stille couplings, radical dehalogenations, radical cyclizations, and carbonyl allylations. Not only could the tin residues be removed from the crude reaction mixture through a phase separation process but also they could be recovered and recycled.