9,10-Dicyanoanthracene

Base Information

• Chemical Name: 9,10-Dicyanoanthracene
• CAS No.: 1217-45-4
• Molecular Formula: C16H8N2
• Molecular Weight: 228.253
• Hs Code.: 29269095
• European Community (EC) Number: 679-755-9
• NSC Number: 17556
• DSSTox Substance ID: DTXSID4061628
• Nikkaji Number: J47.160G
• Wikidata: Q27122536
• Metabolomics Workbench ID: 57690
• Mol file: 1217-45-4.mol

Synonyms:9,10-dicyanoanthracene

Chemical Property of 9,10-Dicyanoanthracene

Chemical Property:

• Appearance/Colour: yellow to golden yellow needles or powder
• Vapor Pressure: 1.16E-09mmHg at 25°C
• Melting Point: 340 °C(lit.)
• Refractive Index: 1.73
• Boiling Point: 487.7 °C at 760 mmHg
• Flash Point: 247.8 °C
• PSA: 47.58000
• Density: 1.28 g/cm³
• LogP: 3.73636
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 228.068748264
• Heavy Atom Count: 18
• Complexity: 345

Purity/Quality:

97% ^*data from raw suppliers

DCA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2C#N)C#N
• General Description: 9,10-Dicyanoanthracene (DCA) is an electron acceptor used in photoinduced electron transfer reactions, facilitating processes such as isomerization, dimerization, and oxygenation of organic compounds like anethole. It promotes the formation of cyclobutane dimers and oxygenated products while quenching isomerization in the presence of oxygen, operating through mechanisms involving cation radicals rather than singlet oxygen or acyclic intermediates.

Technology Process of 9,10-Dicyanoanthracene

There total 84 articles about 9,10-Dicyanoanthracene 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:

Anthracene-9,10-dicarbonitrile; compound with 1,2,3,4,5,6-hexamethyl-benzene (17263-12-6) → 9,10-Dicyanoanthracene (1217-45-4) + Hexamethylbenzene (87-85-4)

Guidance literature:

In acetonitrile; Thermodynamic data; Rate constant; ΔG;

DOI:10.1021/ja00167a027

Reference yield:

Anthracene-9,10-dicarbonitrile; compound with 4,4'-dimethyl-biphenyl → 9,10-Dicyanoanthracene (1217-45-4) + (4,4'-dimethyl-1,1'-biphenyl) (613-33-2)

Guidance literature:

In acetonitrile; Thermodynamic data; Rate constant; ΔG;

DOI:10.1021/ja00167a027

Reference yield:

Anthracene-9,10-dicarbonitrile; compound with 2,6-dimethyl-naphthalene → 9,10-Dicyanoanthracene (1217-45-4) + 2.6-dimethylnaphthalene (581-42-0)

Guidance literature:

In acetonitrile; Thermodynamic data; Rate constant; ΔG;

DOI:10.1021/ja00167a027

upstream raw materials:

C₁₆H₁₄N₄

lead(IV) tetraacetate

Anthracene-9,10-dicarbonitrile; compound with naphthalene

Anthracene-9,10-dicarbonitrile; compound with 2-methyl-naphthalene

Downstream raw materials:

10,10-dibenzyl-9-(4-chloro-benzyl)-9,10-dihydro-anthracene-9-carbonitrile

10,10-dibenzyl-9,10-dihydro-anthracene-9-carbonitrile

fluorene radical cation

Naphthalene

Refernces

Photocyclization and photooxidation of 3-styrylthiophene

10.1016/S0040-4039(00)00097-6

The study focuses on the photocyclization and photooxidation processes of 3-styrylthiophene, a compound with two isomers: trans-3-styrylthiophene (1) and cis-3-styrylthiophene (2). The research investigates how these isomers react under different photochemical conditions, including in nonpolar and polar solvents, with and without sensitizers. The key findings include that cis-3-styrylthiophene (2) undergoes photochemical cis–trans isomerization and cyclization to form dihydronaphtho-[1,2-b]thiophene (3), with a higher quantum efficiency in nonpolar solvents. Dye-sensitized photooxidation of 3-styrylthiophene results in the production of benzaldehyde and 3-thiophenecarboxaldehyde, and the process is suggested to occur via a superoxide radical anion pathway rather than through singlet oxygen. Additionally, auto-photooxidation in the presence of oxygen leads to photocyclization, oxidation, and dimerization products. The study proposes that these reactions may involve the formation of a charge transfer complex between oxygen and the substrate. The research is significant for understanding the behavior of polythiophenes, which are important for the production of conductive polymers, and could contribute to improving the photostability of these materials.

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.