235-92-7

Basic information

• Product Name: 1H-CYCLOPENTA[L]PHENANTHRENE
• Synonyms: 1H-CYCLOPENTA[1]PHENANTHRENE;1H-CYCLOPENTA[L]PHENANTHRENE;1H-Cyclopenta[l]phenanthrene
• CAS NO: 235-92-7
• Molecular Formula: C₁₇H₁₂
• Molecular Weight: 216.28
• Mol File: 235-92-7.mol

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 415.1 °C at 760 mmHg
• Flash Point: 195.4 °C
• Appearance: /
• Density: 1.201 g/cm³
• Vapor Pressure: 1.02E-06mmHg at 25°C
• Refractive Index: 1.754
• CAS DataBase Reference: 1H-CYCLOPENTA[L]PHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-CYCLOPENTA[L]PHENANTHRENE(235-92-7)
• EPA Substance Registry System: 1H-CYCLOPENTA[L]PHENANTHRENE(235-92-7)

Safety Data

• Hazardous Substances Data: 235-92-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1H-Cyclopenta[l]phenanthrene is used as a key intermediate in organic synthesis for the production of complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of various compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1H-Cyclopenta[l]phenanthrene serves as a starting material for the preparation of specific pharmaceuticals. Its chemical properties and structural features enable the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 1H-Cyclopenta[l]phenanthrene is utilized as a precursor for the synthesis of various agrochemicals. Its role in creating effective pesticides and other agricultural chemicals contributes to crop protection and yield enhancement.
Used in Toxicology and Environmental Chemistry Research:
Due to its classification as a potential carcinogen and environmental pollutant, 1H-Cyclopenta[l]phenanthrene is also used in research settings within toxicology and environmental chemistry. It is studied to understand its impact on human health and the environment, as well as to develop methods for its detection, monitoring, and mitigation.

InChI:InChI=1/C17H12/c1-3-8-14-12(6-1)13-7-2-4-9-15(13)17-11-5-10-16(14)17/h1-10H,11H2

Upstream product

• 72471-15-9 ethyl 3,3a-dihydro-3a-hydroxy-2-oxo-2H-cyclopentaphenanthrene-1-carboxylate 
• 72471-16-0 methyl 3,3a-dihydro-3a-hydroxy-2-oxo-2H-cyclopentaphenanthrene-1-carboxylate 
• 37913-11-4 1,3-dihydro-2H-cyclopenta[l]phenanthrene-2-one 
• 117775-61-8 C₂₄H₂₀N₂O₂S 
• 35692-05-8 2,3-dihydro-1H-cyclopenta[l]phenanthrene-2-ol 

Relevant articles and documents

Palladium-catalyzed domino coupling reactions of aryl halides with norbornene and norbornene derivatives - A simple route to polycyclic aromatic compounds

Under palladium-catalysis, norbornene 1, dicyclopentadiene 10, norbornenol 13, and norbornenone 15 react with unsubstituted as well as substituted bromo- and iodobenzenes to give 1 : 3 coupling products with 4-aryl-9,10-dihydrophenanthrene units with up to 70% isolated yields. The structures of two such products 4a and 4e were proved by X-ray crystal structure analysis. 2-Bromothiophene 17 reacts with 1 and 10 to yield a mixture of 2 : 1 and 3 : 1 coupling products, while 3-iodopyridine 22a, 3-iodo-6-methylpyridine 22b and 4-iodopyridine 25 give only 2 : 1 coupling products with 5,6-dihydro-3,8-phenanthroline and 5,6-dihydro-2,9-phenanthroline units, respectively. Some new mechanistic insights into this interesting four-component domino coupling reaction are presented. The products can easily be transformed by photocyclization/dehydrogenation and/or flash vacuum pyrolysis to a variety of cyclopentadiene-anellated polycyclic aromatic compounds in very high yields. The reported sequence also presents the easiest access to benzo[e]pyrene.

1H and 13C Nuclear Magnetic Resonance Reinvestigation of the Dibenzocyclononatetraenyl Anion and Its 5,9-Diphenyl Derivative. Planarity vs Nonplanarity

It is found that the dibenzocyclononatetraenyl anion is readily transformed into the stable 1H-cyclopentaphenanthren-1-yl anion.Earlier reported NMR data of this compound were incorrectly assigned to a planar structure of the dibenzocyclononatetraenyl anion.The nonplanarity of the initially formed nine-membered ring anion was confirmed both experimentally and theoretically.The ring-closure process does not take place in the anion of the 5,9-diphenyl derivative, which retains a nonplanar conformation of the nine-membered ring.