1210-12-4

Usage

Uses

Used in Chemical Research:
9-Anthracenecarbonitrile is used as a research compound for studying the mechanism of charge separation within phenothiazine (PTZH) or phenoxazine (PXZH) systems. It serves as an electron acceptor in these studies, providing insights into the behavior of charge transfer processes.
Used in Photophysical Studies:
The fluorescence excitation spectra of 9-anthracenecarbonitrile have been studied, making it a useful compound for understanding the photophysical properties of similar organic molecules. This knowledge can be applied to the development of new materials and technologies in various fields, such as optoelectronics and photovoltaics.

Purification Methods

Crystallise the nitrile from EtOH or toluene, and sublime it in a vacuum in the dark under N2 [Ebied et al. J Chem Soc, Faraday Trans 1 76 2170 1980, Kikuchi et al. J Phys Chem 91 574 1987]. [Beilstein 9 I 304.]

InChI:InChI=1/C15H9N/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-9H

Upstream product

• 100-25-4 para-dinitrobenzene 
• 1217-45-4 9,10-Dicyanoanthracene 
• 616-39-7 N,N-diethylnmethylamine 
• 10545-36-5 N-<(trimethylsilyl)methyl>-N,N-diethylamine 
• 120-12-7 anthracene 
• 143-33-9 sodium cyanide 
• 1564-64-3 9-Bromoanthracene 
• 716-53-0 9-chloroanthracene 
• 557-21-1 dicyanozinc 
• 85985-44-0 anthracen-9-yl-oxo-acetonitrile 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 723-62-6 anthracen-9-carboxylic acid 
• 93-61-8 N-methyl-N-phenylformamide 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 

Downstream Products

• 33998-38-8 9-cyanoanthracene photodimer 
• 84-65-1 9,10-phenanthrenequinone 
• 65-85-0 benzoic acid 
• 623-26-7 terephthalonitrile 
• 642-31-9 9-anthracene aldehyde 
• 602-60-8 9-nitroanthracene 
• 1213-82-7 9-chloro-10-cyano-anthracene 
• 2476-68-8 9-(aminomethyl)anthracene 
• 97015-27-5 10-benzyl-9,10-dihydro-anthracene-9-carbonitrile 
• 241488-97-1 α-(R)-9'-anthrylethylamine 
• 148065-53-6 (S)-1-(9-anthracenyl)ethylamine 
• 723-62-6 anthracen-9-carboxylic acid 
• 623-26-7 terephthalonitrile radical anion 
• 100-25-4 1,4-dinitroanthracene radical anion 

Relevant academic research and scientific papers

Difluorocarbene-Based Cyanation of Aryl Iodides

A large number of efficient cyanation methods have been developed because of the wide range of applications of nitriles, but conventional methods usually suffer from the need for a toxic cyanation reagent. Although difluorocarbene chemistry has received increasing attention, the use of difluorocarbene as a sources of the nitrile carbon for nitrile groups remains largely unexplored. We describe a difluorocarbene-based cyanation of aryl iodides promoted by a cheap copper source, Cu(NO 3) 2 ·2.5H 2 O, under an air atmosphere. Ph 3 P + CF 2 CO 2-, an easily available and shelf-stable difluorocarbene reagent, and NaNH 2 are used as the carbon source and the nitrogen source for the nitrile group, respectively. The cyanation protocol is attractive because no toxic reagent is used and performing the reactions under an air atmosphere is operationally convenient.

Gallium-containing polymer brush film as efficient supported Lewis acid catalyst in a glass microreactor

Polystyrene sulfonate polymer brushes, grown on the interior of the microchannels in a microreactor, have been used for the anchoring of gallium as a Lewis acid catalyst. Initially, gallium-containing polymer brushes were grown on a flat silicon oxide surface and were characterized by FTIR, ellipsometry, and X-ray photoelectron spectroscopy (XPS). XPS revealed the presence of one gallium per 2-3 styrene sulfonate groups of the polymer brushes. The catalytic activity of the Lewis acid-functionalized brushes in a microreactor was demonstrated for the dehydration of oximes, using cinnamaldehyde oxime as a model substrate, and for the formation of oxazoles by ring closure of ortho-hydroxy oximes. The catalytic activity of the microreactor could be maintained by periodic reactivation by treatment with GaCl3.

Preparation of 14C-labeled multiwalled carbon nanotubes for biodistribution investigations

(Figure Presented) A new method allowing the 14C-labeling of carboxylic acid functions of carbon nanotubes is described. The key step of the labeling process is a decarbonylation reaction that has been developed and optimized with the help of a screening method. The optimized process has been successfully applied to multiwalled carbon nanotubes (MWNTs), and the corresponding 14C-labeled nanotubes were used to investigate their in vivo behavior. Preliminary results obtained after i.v. contamination of rats revealed liver as the main target organ. Radiolabeling of NTs with a long-life radioactive nucleus like 14C, coupled to a highly sensitive autoradiographic method, that provides a unique detection threshold, will make it possible to determine for a long time period whether or not NTs remain in any organs after animal exposure.

Palladium-Catalyzed Synthesis of Aryl Nitriles: Using α-Iminonitrile as Cyano Source for Aryl Halide Cyanations

An efficient and ligand-free palladium-catalyzed exchange reaction to synthesize aryl nitriles by using α-iminonitrile as a starting reagent has been developed. This methodology provides an optional method for the synthesis of aryl nitriles with moderate to good yields. At the same time, this approach is adaptable for many substrates.

Free Enthalpy Dependence of Free Radical Yield of Photoincuced Electron Transfer in Acetonitrile

The free enthalpy dependence of the free-radical yield ΦR of the electron-transfer (ET) fluorescence quenching was studied in acetonitrile by using anthracenecarbonitriles as the electron-accepting fluorescer and 1,4-diphenyl-1,3-butadienes as the electron-donating quencher. ΦR decreases, passes through a minimum, increases with increase of ΔGf, the free enthalpy change involved in the actual ET process, and then suddenly falls when ΔGf goes beyond -0.25 eV.Switchover of the quenching mechanism was suggested for the ET fluorescence quenching: The radical pairs are exclusively produced by the full ET in the encounter state bet ween the fluorescer and the quencher when ΔGf is smaller than -0.4 eV, but in contrast through the partial ET, i.e., the exciplex formation as the primary quenching products when ΔGf is larger than -0.4 eV.

Photochemical cyanation of aromatic hydrocarbons with cyanide anion

The efficient photo-cyanation of phenanthrene and naphthalene with sodium cyanide in the presence of 1,4-dicyanobenzene is reported.

Unusual Base-induced Ring-opening Reactions of the Bis-tosylhydrazones of Dibenzobicyclooctadiene-2,3-dione and Acenaphthenequinone

Unusual KOH-induced ring-opening reactions of the bis-tosylhydrazones of dibenzobicyclooctadiene-2,3-dione and acenaphthenequinone are described.

Preparation of (1R,1′R)-1,1′-(anthracene-9,10-diyl)bis(2,2,2-trifluoroethanamine): a chiral diamine with low basicity

A new chiral diamine with low basicity was synthesized in enantiopure form. (1R,1′R)-1,1′-(Anthracene-9,10-diyl)bis(2,2,2-trifluoroethanamine) was obtained by means of several stereochemically controlled reactions. The structures of the title compound and several intermediates were studied.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.

Cu2O-Catalyzed Conversion of Benzyl Alcohols Into Aromatic Nitriles via the Complete Cleavage of the C≡N Triple Bond in the Cyanide Anion

Nitrogen transfer from cyanide anion to an aldehyde is emerging as a promising method for the synthesis of aromatic nitriles. However, this method still suffers from a disadvantage that a use of stoichiometric Cu(II) or Cu(I) salts is required to enable the reaction. As we report herein, we overcame this drawback and developed a catalytic method for nitrogen transfer from cyanide anion to an alcohol via the complete cleavage of the C≡N triple bond using phen/Cu2O as the catalyst. The present condition allowed a series of benzyl alcohols to be smoothly converted into aromatic nitriles in moderate to high yields. In addition, the present method could be extended to the conversion of cinnamic alcohol to 3-phenylacrylonitrile.