9-Anthracenecarbonitrile

Base Information

• Chemical Name: 9-Anthracenecarbonitrile
• CAS No.: 1210-12-4
• Molecular Formula: C15H9N
• Molecular Weight: 203.243
• Hs Code.: 2926909090
• European Community (EC) Number: 214-909-7
• NSC Number: 26997
• UNII: 6D39005L8T
• DSSTox Substance ID: DTXSID3049209
• Nikkaji Number: J127I
• Wikidata: Q27264531
• ChEMBL ID: CHEMBL3185506
• Mol file: 1210-12-4.mol

Synonyms:9-cyanoanthracene

Chemical Property of 9-Anthracenecarbonitrile

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 4.67E-07mmHg at 25°C
• Melting Point: 173-177 °C(lit.)
• Refractive Index: 1.719
• Boiling Point: 413.794 °C at 760 mmHg
• Flash Point: 205.393 °C
• PSA: 23.79000
• Density: 1.208 g/cm₃
• LogP: 3.86468
• Water Solubility.: Insoluble in water.
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 203.073499291
• Heavy Atom Count: 16
• Complexity: 278

Purity/Quality:

97% ^*data from raw suppliers

9-Cyanoanthracene >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C#N
• Uses: Anthracene-9-carbonitrile was used to study the mechanism of charge separation within phenothiazine (PTZH) or phenoxazine (PXZH), and 9-cyanoanthracene(electron acceptor). Also it has been used to study the fluorescence excitation spectra of this compound . 9-Anthracenecarbonitrile was used to study the mechanism of charge separation within phenothiazine (PTZH) or phenoxazine (PXZH), and 9-cyanoanthracene(electron acceptor).

Technology Process of 9-Anthracenecarbonitrile

There total 76 articles about 9-Anthracenecarbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

anthracene (120-12-7) + N-methyl-N-phenylformamide (93-61-8) → 9-cyanoanthracene (1210-12-4)

Guidance literature:

N-methyl-N-phenylformamide; With pyrophosphoryl chloride; at 0 ℃; for 0.5h;

anthracene; In N,N-dimethyl-formamide; at 100 ℃; for 10h;

With ammonia; iodine; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 20 ℃; for 3h; regioselective reaction;

DOI:10.1016/j.tet.2012.04.034

Reference yield: 95.0%

9-anthracene aldehyde (642-31-9) → 9-cyanoanthracene (1210-12-4)

Guidance literature:

With HCl·DMPU; hydroxylamine hydrochloride; In acetonitrile; at 60 ℃;

DOI:10.1039/d0gc00757a

Reference yield: 94.0%

9-anthracenealdehyde oxime (18004-57-4) → 9-cyanoanthracene (1210-12-4)

Guidance literature:

9-anthracenealdehyde oxime; With 2-chloro-1-methyl-pyridinium iodide; In dichloromethane; at 20 ℃; for 0.166667h;

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1081/SCC-120034158

upstream raw materials:

bromocyane

anthracene

(Z)-anthracene-9-carbaldehyde oxime

(E)‐anthracene‐9‐carbaldehyde oxime

Downstream raw materials:

9-cyanoanthracene photodimer

9,10-phenanthrenequinone

benzoic acid

terephthalonitrile

Refernces

Electron Transfer Induced Photoisomerization, Dimerization, and Oxygenation of trans- and cis-Anethole. The Role of Monomer and Dimer Cation Radicals

10.1021/ja00234a014

The study investigates the photoinduced electron transfer reactions of trans-anethole (t-A) and cis-anethole (c-A), focusing on their isomerization, dimerization, and oxygenation processes. When irradiated in the presence of electron acceptors like 9-cyanoanthracene (CA) or 9,10-dicyanoanthracene (DCA), both t-A and c-A undergo trans,cis isomerization and dimerization to form various cyclobutane dimers, with the dimer ratio being sensitive to reaction conditions. The presence of oxygen quenches isomerization and dimerization, leading to the formation of oxygenated products like p-anisaldehyde. The study concludes that isomerization occurs via reverse electron transfer to generate triplet anethole, while dimerization proceeds via quasi-concerted [2 + 1] cycloaddition of cation radicals. The results also suggest that an acyclic 1,4-cation radical is not involved in these reactions, as no [2 + 4] dimers or 1,2-dioxanes are detected.