5,12-Naphthacenequinone

Base Information

• Chemical Name: 5,12-Naphthacenequinone
• CAS No.: 1090-13-7
• Molecular Formula: C18H10O2
• Molecular Weight: 258.276
• Hs Code.: 29146990
• European Community (EC) Number: 214-127-6
• NSC Number: 401183
• UNII: 34XLX2VR6G
• DSSTox Substance ID: DTXSID7061483
• Nikkaji Number: J120A
• Wikidata: Q27122531
• Metabolomics Workbench ID: 57685
• Mol file: 1090-13-7.mol

Synonyms:5,12-naphthacenequinone;5,12-NpQ

Chemical Property of 5,12-Naphthacenequinone

Chemical Property:

• Appearance/Colour: Khaki powder
• Vapor Pressure: 4.24E-09mmHg at 25°C
• Melting Point: 282-286 °C (dec.)(lit.)
• Refractive Index: 1.722
• Boiling Point: 472.5 °C at 760 mmHg
• Flash Point: 175.5 °C
• PSA: 34.14000
• Density: 1.336 g/cm³
• LogP: 3.61520
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly, Heated), DMF (Slightly, Heated), DMSO (Slightly, Heated)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 258.068079557
• Heavy Atom Count: 20
• Complexity: 387

Purity/Quality:

98%,99%, ^*data from raw suppliers

5,12-Napthacenequinone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)C(=O)C4=CC=CC=C4C3=O
• Uses: 5,12-Naphthacenequinone was used to study the phototransformation of phenol in aqueous solution.

Technology Process of 5,12-Naphthacenequinone

There total 58 articles about 5,12-Naphthacenequinone 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: 95.0%

C24H16O4 → 5,12-naphthacenequinone (1090-13-7)

Guidance literature:

With triethylamine; In chloroform; at 20 ℃; for 1h;

DOI:10.1016/j.crci.2014.01.024

Reference yield: 80.0%

1,4-Dihydroxynaphthalene (571-60-8) + o-phthalic dicarboxaldehyde (643-79-8) → 5,12-naphthacenequinone (1090-13-7)

Guidance literature:

With sodium carbonate; In 2,2,2-trifluoroethanol;

DOI:10.1021/ol049695p

Reference yield: 78.0%

o-phthalic dicarboxaldehyde (643-79-8) + [1,4]naphthoquinone (130-15-4) → 5,12-naphthacenequinone (1090-13-7)

Guidance literature:

With triethylsilane; scandium tris(trifluoromethanesulfonate); In toluene; at 135 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol201479p

upstream raw materials:

phthalic anhydride

3-benzoyl-2-naphthoic acid

Perbenzoic acid

chloroform

Downstream raw materials:

5,12-diphenyl-5,12-dihydro-naphthacene-5,12-diol

Tetracen

5,12-bis(phenylethynyl)naphthacene

5,12-dihydro-naphthacene

Refernces

• 1、 Reichwagen, Jens,Hopf, Henning,Del Guerzo, Andre,Desvergne, Jean-Pierre,Bouas-Laurent, Henri. "Photodimers of a soluble tetracene derivative. Excimer fluorescence from the head-to-head isomer". . p. 1899 - 1902. Retrieved 2004.
• 2、 Dennis, David G.,Okumura, Mikiko,Sarlah, David. "Synthesis of (±)-Idarubicinone via Global Functionalization of Tetracene". . p. 10193 - 10198. Retrieved 2019.
• 3、 Fatiadi. "-". . p. 1087. Retrieved 1967.
• 4、 Odom, Susan A.,Parkin, Sean R.,Anthony, John E.. "Tetracene Derivatives as Potential Red Emitters for Organic LEDs". . p. 4245 - 4248. Retrieved 2003.
• 5、 Smith, James G.,Dibble, Peter W.. "2-(Dimethoxymethyl)benzyl Alcohol: A Convenient Isobenzofuran Precursor". . p. 5361 - 5362. Retrieved 1983.
• 6、 Filatov, Mikhail A.,Etzold, Fabian,Gehrig, Dominik,Laquai, Frédéric,Busko, Dmitri,Landfester, Katharina,Baluschev, Stanislav. "Interplay between singlet and triplet excited states in a conformationally locked donor-acceptor dyad". . p. 19207 - 19217. Retrieved 2015.
• 7、 Kitaguchi, Nobuya. "Effects of Substituents and Solvents on the Electronic Spectra of 9,10-Dihydro-9,10-o-benzenoanthracene-1,4-diones: Intramolecular Charge Transfer". . p. 800 - 807. Retrieved 1989.
• 8、 Kimoto, Takakazu,Tanaka, Kenro,Kawahata, Masatoshi,Yamaguchi, Kentaro,Otsubo, Saika,Sakai, Yoshimasa,Ono, Yuuki,Ohno, Akira,Kobayashi, Kenji. "Bis(methylthio)tetracenes: Synthesis, crystal-packing structures, and OFET properties". . p. 5018 - 5025. Retrieved 2011.