9,10-Phenanthrenequinone

Base Information

• Chemical Name: 9,10-Phenanthrenequinone
• CAS No.: 84-11-7
• Molecular Formula: C14H8O2
• Molecular Weight: 208.216
• Hs Code.: 29146990
• European Community (EC) Number: 201-515-5
• NSC Number: 10446,7389
• UNII: 42L7BZ8H74
• DSSTox Substance ID: DTXSID3058901
• Nikkaji Number: J3.878D
• Wikipedia: Phenanthrenequinone
• Wikidata: Q25103737
• Pharos Ligand ID: JJA97P5N4HNR
• Metabolomics Workbench ID: 52189
• ChEMBL ID: CHEMBL51931
• Mol file: 84-11-7.mol

Synonyms:9,10-phenanthraquinone;9,10-phenanthrenedione;9,10-phenanthrenequinone;9,10-phenanthroquinone

Chemical Property of 9,10-Phenanthrenequinone

Chemical Property:

• Appearance/Colour: burnt-orange powder
• Vapor Pressure: 2.29E-05mmHg at 25°C
• Melting Point: 209-212 °C(lit.)
• Refractive Index: 1.659
• Boiling Point: 359.999 °C at 760 mmHg
• Flash Point: 163.142 °C
• PSA: 34.14000
• Density: 1.309 g/cm³
• LogP: 2.73260
• Storage Temp.: 2-8°C
• Solubility.: 7.5mg/l
• Water Solubility.: Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 208.052429494
• Heavy Atom Count: 16
• Complexity: 289

Purity/Quality:

99% ^*data from raw suppliers

9,10-Phenanthrenequinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C(=O)C2=O
• Description: 9,10-phenanthrenequinone (9,10-PQ) is a quinone molecule found in air pollution abundantly in the diesel exhaust particles (DEP). This compound has studied extensively and has been shown to develop cytotoxic effects both in vitro and in vivo. 9, 10-PQ has been proposed to play a critical role in the development of cytotoxicity via generation of reactive oxygen species (ROS) through redox cycling. This compound also reduces expression of glutathione (GSH), which is critical in Phase II detoxification reactions.
• Uses: 9,10-Phenanthrenequinon may be used for high quality passivation on silicon (100) surfaces. Quinones may serve as substrates for a variety of flavoenzymes. The quinones of polycyclic aromatic hydrocarbons are present in abundance in all burnt organic material. On being used to passivate silicon surfaces, it reacts with the dangling bonds on the surface via a heteroatomic Diels-Alder reaction. On account of the Π-electron conjugation, the semi conducting nature of the silicon is unaffected. 9,10-Phenanthrenequinone is used in the formation of spirophosphoranes containing acyclic 5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl substituent. 9,10-Phenanthrenequinon may be used for high quality passivation on silicon (100) surfaces. Quinones may serve as substrates for a variety of flavoenzymes.

Technology Process of 9,10-Phenanthrenequinone

There total 214 articles about 9,10-Phenanthrenequinone 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: 79.0%

phenanthrene-9,10-oxide (585-08-0,84489-06-5) → 9-Phenanthrol (484-17-3) + 9,10-phenanthrenequinone (84-11-7)

Guidance literature:

for 1h; Irradiation; in air;

DOI:10.1248/cpb.30.4500

Reference yield: 56.0%

phenanthrene (85-01-8) → phthalic anhydride (85-44-9) + biphenyl-2,2'-dicarboxylic acid anhydride (6050-13-1) + 9,10-phenanthrenequinone (84-11-7)

Guidance literature:

With ruthenium trichloride; sodium periodate; In dichloromethane; water; acetonitrile; at 21.84 ℃; for 4h;

DOI:10.1002/chem.201800423

Reference yield: 21.0%

phenanthrene (85-01-8) → 9-Phenanthrol (484-17-3) + rac-10,10'-dihydroxy-9,9'-biphenanthryl (95033-74-2,95033-75-3,110071-78-8) + 9,10-phenanthrenequinone (84-11-7)

Guidance literature:

With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide; In acetonitrile; for 0.666667h; Irradiation;

DOI:10.1248/cpb.38.2676

upstream raw materials:

ethanol

10-hydroxy-10-(2-oxopropyl)-9,10-dihydrophenanthren-9-one

9,10-dihydro-10,10-dichlorophenanthren-9-one

sodium phenoxide

Downstream raw materials:

2-phenyl-phenanthro[9,10-d][1,3]dioxole

phenanthro[9,10-g]pteridine-11,13(10H,12H)-dione

10,15-Diphenyl-10,15-dihydro-10,15-epoxido-benzo[f]phenanthro[9,10-b][1,4]dioxocin

9,10-Phenanthroimidazol

Refernces

• 1、 Farrell, David,Kingston, Samuel J.,Tungulin, Dmitry,Nuzzo, Stefano,Twamley, Brendan,Platts, James A.,Baker, Robert J.. "N-Aryl-9,10-phenanthreneimines as Scaffolds for Exploring Noncovalent Interactions: A Structural and Computational Study". . p. 5597 - 5609. Retrieved 2017.
• 2、 Japp. "". . . Retrieved 1879.
• 3、 Maruyama et al.. "-". . p. 2777. Retrieved 1977.
• 4、 Abdellattif, Magda H.,Alsaeedi, Mona S.,Babgi, Bandar A.,Humphrey, Mark G.,Hussien, Mostafa A.. "DNA-binding and anticancer activity of binuclear gold(I) alkynyl complexes with a phenanthrenyl bridging ligand". . . Retrieved 2020.
• 5、 Bors, István,Purgel, Mihály,Fehér, Péter Pál,Varga, Tamás,Speier, Gábor,Korecz, László,Kaizer, József. "Unexpected radical mechanism in a [4+1] cycloaddition reaction". supporting information. p. 8440 - 8444. Retrieved 2021/05/25.
• 6、 Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi. "Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes". supporting information. p. 15793 - 15798. Retrieved 2020/10/12.