243-17-4

Usage

Uses

Used in Environmental Analysis:
2,3-Benzofluorene is used as a standard in the three-way analysis of fluorescence excitation-emission matrices of mixtures of polycyclic aromatic hydrocarbons (PAHs). This application aids in the detection and analysis of these compounds in environmental samples.
Used in Air Quality Monitoring:
In the field of air quality monitoring, 2,3-benzofluorene is utilized as a standard to detect ambient particle-bound polycyclic aromatic hydrocarbons using a real-time aerosol mass spectrometer. This helps in assessing the presence and concentration of PAHs in the atmosphere, which are known to have potential health risks.
Used in Chemical Research:
Due to its unique chemical properties, 2,3-benzofluorene can be employed in various chemical research applications, particularly in the study of PAHs and their interactions with other compounds. This can contribute to the development of new methods for environmental monitoring and the understanding of the effects of PAHs on human health and the environment.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 904, 1988 DOI: 10.1021/jo00239a050

Carcinogenicity

Benzo[b]fluoranthene gave a positive result in one two-stage carcinogenesis test in mice.

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

Upstream product

• 16096-10-9 8,9-dihydrobenzo[b]fluorene 
• 3074-03-1 11H-Benzo[b]fluoren-11-one 
• 579-74-8 2-Methoxyacetophenone 
• 286-85-1 1H-cyclopropa[b]naphthalene 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 98-86-2 acetophenone 
• 611-70-1 phenyl isopropyl ketone 
• 7647-01-0 hydrogenchloride 
• 61895-27-0 2,2'-spirobiindan-1,1'-dione 
• 110334-50-4 11H-benzo[b]fluoren-11-ol 
• 860560-68-5 7,8,9,11-tetrahydro-6H-benzo[b]fluorene 
• 83-33-0 inden-1-one 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 728-17-6 benzo[b]fluorene cesium salt 
• 203-64-5 4H-Cyclopenta[def]phenanthrene 
• 3112-88-7 Benzyl phenyl sulfone 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 107643-23-2 C₂₆H₁₉NO₄ 
• 107643-24-3 C₂₆H₁₉NO₄ 
• 107643-25-4 C₂₇H₂₂O₃ 
• 107643-26-5 C₂₇H₂₂O₃ 
• 107643-21-0 C₂₆H₂₀O₂ 
• 107643-22-1 C₂₆H₂₀O₂ 
• 205-99-2 benzo[e]acephenanthrylene 

Relevant academic research and scientific papers

Mechanistic Study of Domino Processes Involving the Bidentate Lewis Acid Catalyzed Inverse Electron-Demand Diels?Alder Reaction

The detailed understanding of mechanisms is the basis to design new reactions. Herein, we studied the domino bidentate Lewis acid catalyzed inverse electron-demand Diels?Alder (IEDDA) reaction developed in our laboratory computationally as well as by synthetic experiments, to characterize different pathways. A quinodimethane intermediate was identified as key structure, which is the basis for all subsequent transformations: Elimination to an aromatic naphthalene, rearrangement to a dihydroaminonaphthalene and a photo-induced ring opening. These insights allow to optimize the reaction conditions, such as catalytic utilization of amine, as well as to advance new reactions in the future.

Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels-Alder Reaction Followed by Photoinduced Ring-Opening

The combination of a Lewis acid-catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction with a photoinduced ring-opening (PIRO) reaction in a domino process has been established as an efficient synthetic method to access medium-sized carbocycles. From readily available electron-rich and electron-poor phthalazines and enamines, respectively, as starting materials, various 9- and 11-membered carbocycles were prepared. This versatile transition-metal-free tool will be valuable for broadening the structural space in biologically active compounds and functional materials.

ORGANIC ELECTROLUMINESCENT DEVICE

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device of the present disclosure can provide a low driving voltage and excellent luminous efficiency by comprising a specific combination of a host compound and a hole transport material.

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having excellent luminous properties can be produced.

Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp2)-H Bond Functionalization

A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C-C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source. Metal carbene migratory insertion and C(sp2)-H bond activation are proposed as the key steps in this transformation. The reaction further demonstrates the versatility of the carbene-based coupling in combination with various transition-metal-catalyzed transformations.

Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. (Figure presented.).

Palladium-Catalyzed Reaction of Haloarenes with Diarylethynes: Synthesis, Structural Analysis, and Properties of Methylene-Bridged Arenes

Fluorenes and methylene-bridged polyarenes were easily and efficiently synthesized from haloarenes (or aryl triflates) and diarylethynes by a one-pot, two-step procedure. This protocol involves the palladium-catalyzed cycloisomerization and a subsequent base-mediated retro-aldol condensation. A major advantage is that the starting materials need not have ortho functional groups to complete the annulation. The backbone of the designed products was enlarged using dihaloarenes, highly π-conjugated haloarenes, or diarylalkynes. The mechanism of the formation of benzo[a]fluorene was investigated. The bowl-shaped structure of methylene-bridged indenocorannulene was verified by X-ray crystallography. The photophysical and electrochemical properties of the products thus prepared were investigated.

Ion pair pKs of some amines: Extension of the computed lithium pK scale

The pK of p-(methylamino)biphenyl, 1, on our Li scale, pK(Li) = 22.09, compared to the cesium scale, pK(Cs) = 28.60. For hexamethyldisilazane, HMDS, pK(Li) = 23.05, pK(Cs) = 29.26. These results are those for the monomers in THF; corrections were made for dimers present in some cases. The pK(Li) of these two amines fit well the previously found correlation with Hartree-Fock calculations at 6-31+g(d) using RLi coordinated with three dimethyl ethers as a computational model for RLi in THF. The results are also compared with earlier pK(Li)s reported from equilibria with lithium amides in which aggregation was not considered.

Bidentate Lewis acids for the activation of 1,2-diazines - A new mode of catalysis

Bidentate Lewis acids were applied as catalysts for the inverse-electron-demand Diels-Alder (IEDDA) reaction of 1,2-diazines. The concept of catalysis is based on the coordination of the bidentate Lewis acid to both nitrogen atoms of the 1,2-diazine moiety, thereby reducing the electron density and lowering the energy of the LUMO. This should, according to frontier molecular orbital (FMO) theory, facilitate the cycloaddition step. This new concept was successfully applied to a variety of dienophiles and substituted phthalazine substrates. Careful investigations of the mechanism led to the isolation and characterization of key intermediates; all of which support the presented catalytic cycle. Copyright

Synthesis of methylene-bridge polyarenes through palladium-catalyzed activation of benzylic carbon-hydrogen bond

In the presence of palladium(II) acetate [Pd(OAc)2] and an N-heterocyclic carbene (NHC) ligand, fluorene derivatives can be generated in good to excellent yields from 2-halo-2′-methylbiaryls through the benzylic C-H bond activation (14 examples; 81-97% yields). The scope and limitations of this protocol have been examined. A wide range of functional groups, such as alkyl, alkoxy, ester, nitrile, and others, is able to tolerate the reaction conditions herein. The cyclization of an isotope-labelled biphenyl gave the corresponding product with a primary kinetic isotope effect (k H/kD=4.8:1), which indicates that the rate-determining step of this reaction is the activation of the benzylic C-H bond. Moreover, indenofluorenes were also accessed in excellent results from terphenyls (3 examples; 91-92% yields). The cascade reaction of 2,6-dichloro-2′- methylbiphenyl with diphenylacetylene produced 8,9-diphenyl-4H-cyclopenta[def] phenanthrene in 60% yield through the activation of an aryl and a benzylic C-H bond. Copyright