4H-Cyclopenta[def]phenanthren-4-one

Base Information

• Chemical Name: 4H-Cyclopenta[def]phenanthren-4-one
• CAS No.: 5737-13-3
• Molecular Formula: C15H8O
• Molecular Weight: 204.228
• NSC Number: 132541
• UNII: D32SLO7BUV
• DSSTox Substance ID: DTXSID50205967
• Nikkaji Number: J503.671B
• Wikidata: Q63408820
• Mol file: 5737-13-3.mol

Synonyms:4H-Cyclopenta[def]phenanthren-4-one;5737-13-3;4H-CYCLOPENTA(DEF)PHENANTHREN-4-ONE;CCRIS 5798;D32SLO7BUV;NSC 132541;NSC-132541;tetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6,8(13),9,11-heptaen-15-one;NSC132541;UNII-D32SLO7BUV;C15H8O;SCHEMBL5400415;DTXSID50205967;4,5-PHENANTHRYLENE KETONE;C15-H8-O;4H-cyclopenta[def]phenanthrene-4-one;4H-Cyclopenta[def]phenanthren-4-one #;LS-188359;FT-0635830;Q63408820

Chemical Property of 4H-Cyclopenta[def]phenanthren-4-one

Chemical Property:

• Vapor Pressure: 5.54E-07mmHg at 25°C
• Melting Point: 170 °C
• Refractive Index: 1.832
• Boiling Point: 411.6 °C at 760 mmHg
• Flash Point: 185.9 °C
• PSA: 17.07000
• Density: 1.381 g/cm³
• LogP: 3.38200
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 204.057514874
• Heavy Atom Count: 16
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

4H-Cyclopenta[def]phenanthren-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C(=O)C4=CC=CC(=C43)C=C2
• Uses: 4H-Cyclopenta[def]phenanthren-4-one is a ketone-bridged derivative of phenanthrene with mutagenic and carcinogenic activity.

Technology Process of 4H-Cyclopenta[def]phenanthren-4-one

There total 15 articles about 4H-Cyclopenta[def]phenanthren-4-one 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: 85.0%

4H-Cyclopenta[def]phenanthrene (203-64-5) → cyclopenta[def]phenanthren-4-one (5737-13-3)

Guidance literature:

With chromium(VI) oxide; tert.-butylhydroperoxide; In dichloromethane;

DOI:10.1021/jo00049a045

Reference yield: 56.0%

8,9-dihydro-4H-cyclopenta[def]phenanthrene (27410-55-5) → 4H-Cyclopenta[def]phenanthrene (203-64-5) + cyclopenta[def]phenanthren-4-one (5737-13-3) + 4H-cyclopentaphenanthrene-8,9-dione (27018-91-3)

Guidance literature:

With sodium dichromate; In acetic acid; for 0.75h; Heating;

DOI:10.1246/bcsj.53.1179

Reference yield: 35.0%

phenanthrene-4,5-dicarboxylic acid (5462-82-8) → cyclopenta[def]phenanthren-4-one (5737-13-3)

Guidance literature:

phenanthrene-4,5-dicarboxylic acid; With sodium hydroxide; In water; Inert atmosphere; Schlenk technique;

With barium hydroxide octahydrate; In water; Inert atmosphere; Schlenk technique;

at 400 ℃; for 1h; under 0.3 Torr;

DOI:10.1039/c7tc02254a

upstream raw materials:

phenanthrene-4-carboxylic acid

4H-Cyclopenta[def]phenanthrene

8,9-dihydro-4H-cyclopenta[def]phenanthrene

acetic acid

Downstream raw materials:

1-azapyren-2(1H)-one

4H-Cyclopenta[def]phenanthrene

benzo

naphtho<1,8,7-ghi>chrysene

8-Nitro-4H-cyclopentaphenanthren-4-one

Refernces

• 1、 Filippov, Dmitri V.,Overkleeft, Hermen S.,Schneider, Grégory F.,van der Ham, Alex. "A Three-Step Synthesis of 4H-Cyclopenta[def]phenanthrene from Pyrene". supporting information. p. 2013 - 2017. Retrieved 2021/06/25.
• 2、 Kim, Hee Un,Kim, Ji-Hoon,Suh, Hongsuk,Kwak, Jeonghun,Kim, Dongwook,Grimsdale, Andrew C.,Yoon, Sung Cheol,Hwang, Do-Hoon. "High open circuit voltage organic photovoltaic cells fabricated using 9,9′-bifluorenylidene as a non-fullerene type electron acceptor". supporting information. p. 10950 - 10952. Retrieved 2013/11/19.