4H-Cyclopenta[def]phenanthrene

Base Information

• Chemical Name: 4H-Cyclopenta[def]phenanthrene
• CAS No.: 203-64-5
• Molecular Formula: C15H10
• Molecular Weight: 190.244
• Hs Code.: 2902909090
• European Community (EC) Number: 205-905-6
• NSC Number: 88888
• UNII: U16R456Q1Y
• DSSTox Substance ID: DTXSID1024887
• Nikkaji Number: J34.897J
• Wikidata: Q27290553
• ChEMBL ID: CHEMBL1491899
• Mol file: 203-64-5.mol

Synonyms:203-64-5;Methylenephenanthrene;4H-Cyclopenta[def]phenanthrene;4,5-METHYLENEPHENANTHRENE;4H-Cyclopenta(def)phenanthrene;4,5-Phenanthrylenemethane;Benzo(def)fluorene;Benzo[def]fluorene;Cyclopenta[d,e,f]phenanthrene;Methane, 4,5-phenanthrylene-;Phenanthrene, 4,5-methylene-;4-H-Cyclopenta(d,e,f)phenanthrene;NSC 88888;CCRIS 5797;EINECS 205-905-6;BRN 2043908;UNII-U16R456Q1Y;AI3-52512;DTXSID1024887;U16R456Q1Y;NSC-88888;4-05-00-02409 (Beilstein Handbook Reference);4-H-CYCLOPENTA[D,E,F]PHENANTHRENE;Methane,5-phenanthrylene-;Phenanthrene,5-methylene-;4,5-Methylene-phenanthrene;BIDD:GT0431;DTXCID204887;CHEMBL1491899;NSC88888;Tox21_201057;Cyclopenta[d,e,f]phenanthrene, 97%;LS-986;MFCD00003804;AKOS015916260;WLN: L566 B6 2AB O DHJ;NCGC00091166-01;NCGC00091166-02;NCGC00258610-01;CAS-203-64-5;FT-0631866;J-013243;Q27290553;tetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6,8(13),9,11-heptaene

Chemical Property of 4H-Cyclopenta[def]phenanthrene

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 7.52E-05mmHg at 25°C
• Melting Point: 113-115 ºC(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 353 ºC(lit.)
• Flash Point: 168.8 ºC
• PSA: 0.00000
• Density: 1.257 g/cm³
• LogP: 3.89720
• Water Solubility.: 1.1mg/L(27 oC)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 190.078250319
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

Cyclopenta[d,e,f]phenanthrene 97% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2=CC=CC3=C2C4=C(C=CC=C41)C=C3
• Uses: Cyclopenta[d,e,f]phenanthrene (4,5-methylenephenanthrene) has been used as an indicator in the synthesis of homopolymers and block copolymers of styrene and dienes with variable 1,2-polydiene content.

Technology Process of 4H-Cyclopenta[def]phenanthrene

There total 50 articles about 4H-Cyclopenta[def]phenanthrene 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: 65.0%

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

Guidance literature:

With aluminum (III) chloride; sodium tetrahydroborate; In tetrahydrofuran; at 70 ℃; for 3h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.202100190

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: 31.0%

2,6-di-t-butyl-4H-cyclopentaphenanthren-8-ol (117139-25-0) → 4H-Cyclopenta[def]phenanthrene (203-64-5) + 2-tert-Butyl-4H-cyclopenta[def]phenanthrene + 2,6-di-t-butyl-4H-cyclopentaphenanthrene

Guidance literature:

With phosphorus; aluminium trichloride; hydrogen iodide; Yield given. Multistep reaction; 1.) Ac₂O, reflux, 90 h; 2.) toluene, rt., 1.5 h;

DOI:10.1246/bcsj.61.995

upstream raw materials:

cyclopenta[def]phenanthren-4-one

4-methyl-phenanthrene-1,2-dicarboxylic acid-anhydride

1-hydroxy-2.3.3a.4-tetrahydro-1H-cyclopenta[def]phenanthrene

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

Downstream raw materials:

C₂₇H₁₆Br₂

C₂₇H₁₆Br₂O

Refernces

• 1、 Minabe, Masahiro,Yoshida, Masaaki,Takayanagi, Tokuei. "A Facile Synthesis of 4H-Cyclopentaphenanthrene". . p. 995 - 996. Retrieved 1988.
• 2、 Filippov, Dmitri V.,Overkleeft, Hermen S.,Schneider, Grégory F.,van der Ham, Alex. "A Three-Step Synthesis of 4H-Cyclopenta[def]phenanthrene from Pyrene". . p. 2013 - 2017. Retrieved 2021.
• 3、 -. "Condensed compound and organic light emitting diode comprising the same". . . Retrieved 2016/12/01.