343-43-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluorofluorene is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with improved efficacy and selectivity. Its presence in the molecular structure can modulate the pharmacokinetic and pharmacodynamic properties of the resulting compounds, enhancing their therapeutic potential.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Fluorofluorene serves as a crucial building block for the creation of novel agrochemicals, including pesticides and herbicides. Its incorporation into these compounds can lead to enhanced performance and selectivity, contributing to more effective and environmentally friendly agricultural practices.
Used in Organic Synthesis:
2-Fluorofluorene is utilized as a versatile building block in organic synthesis, allowing chemists to construct complex organic compounds with diverse applications. Its unique chemical properties facilitate the formation of new bonds and the synthesis of target molecules, making it an indispensable tool in the development of advanced materials and compounds.
Used in Research and Development:
2-Fluorofluorene is employed as a reagent in research and development laboratories, where it aids in the synthesis of complex organic compounds for various applications. Its unique structure and reactivity make it a valuable asset in the exploration of new chemical pathways and the discovery of innovative materials with potential uses across multiple industries.

Upstream product

• 86-73-7 9H-fluorene 
• 343-01-1 2-fluoro-9H-fluoren-9-one 
• 124-38-9 carbon dioxide 
• 153-78-6 2-aminofluorene 
• 1190085-13-2 2-(chloromethyl)-4-fluoro-1,1'-biphenyl 
• 139911-29-8 4-fluoro-2-methylphenylboronic acid 
• 583-53-9 2,3-dibromobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1073-06-9 3-fluorobromobenzene 
• 60081-02-9 (2-bromophenyl)(3-fluorophenyl)methanol 
• 89346-54-3 2-bromo-4’-fluoro-1,1’-biphenyl 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 1806-25-3 2-fluoro-7-nitro-fluorene 
• 363-16-6 7-fluoro-fluoren-2-ylamine 
• 343-01-1 2-fluoro-9H-fluoren-9-one 
• 6344-64-5 2-Fluoro-9-bromo-fluoren 
• 63283-55-6 (7-Fluoro-9H-fluoren-2-yl)-phenyl-methanone 
• 523-41-1 2-Fluor-phenanthren 
• 97677-19-5 AL 1567 
• 2443-58-5 2-hydroxyfluorene 
• 1989-33-9 9H-fluorene-9-carboxylic acid 
• 1806-21-9 2-fluoro-7-bromofluorene 
• 2195-50-8 2,7-difluoro-9-fluorene 
• 63242-30-8 2-(Chloro-phenyl-methyl)-7-fluoro-9H-fluorene 

Relevant academic research and scientific papers

Solid-state construction of zigzag periphery: Via intramolecular C-H insertion induced by alumina-mediated C-F activation

Caryl-F bond activation has become an important and quickly developing method for construction of carbon-based materials. We report that alumina-mediated C-F bond activation (AmCFA) enables construction of PAHs with zigzag periphery. This method includes

Further lead optimization on Bax activators: Design, synthesis and pharmacological evaluation of 2-fluoro-fluorene derivatives for the treatment of breast cancer

To further pursue potent Bax activators with better safety profiles for the treatment of breast cancer, structural optimization was conducted based on lead compound CYD-4-61 through several strategies, including scaffold hopping on the 2-nitro-fluorene ring, replacement of the nitro group with bioisosteres to avoid potential toxicity, and further optimization on the upper pyridine by exploring diverse alkylamine linkers as a tail or replacing the pyridine with bioisosteric heterocycles. F-containing compound 22d (GL0388) exhibited a good balance between the activity and toxicity, displaying submicromolar activities against a variety of cancer cell lines with 5.8–10.7-fold selectivity of decreased activity to MCF-10A human mammary epithelial cell line. Compound 22d dose-dependently blocked colony formation of breast cancer cells and prevented the migration and invasion of MDA-MB-231 cells. Mechanism of action studies indicate that 22d activated Bax, rendering its insertion into mitochondrial membrane, thereby leading to cytochrome c release from the mitochondria into the cytoplasm, subsequently inducing release of apoptotic biomarkers. Further in vivo efficacy studies of 22d in human breast cancer xenografts arisen from MDA-MB-231 cells demonstrated that this drug candidate significantly suppressed tumor growth, indicating the therapeutic promise of this class of compounds for the treatment of breast cancer as well as the potential for developing F-radiolabeled imaging ligands as anticancer chemical probes.

A comprehensive study of substituent effects on poly(dibenzofulvene)s

We herein report the first cross comparison of 14 poly(dibenzofulvene) derivatives (13 novel examples and the parent poly(dibenzofulvene)) in order to understand how the choice of substituent affects the physical properties of this interesting class of semiconducting polymers. Electron withdrawing substituents decreased the polymerization reactivity and resulted in very low molecular-weight products. Di-substituted poly(dibenzofulvene)s were found to be much less soluble than the mono-analogues which can be explained by the Hansen solubility parameter system. Analysis based on absorption, emission and electrochemistry profiles suggests that polymer solubility is a very important factor that controls the degree of stacking present in the polymer due to synthetic issues. For the first time, the thermal analysis of the parent poly(dibenzofulvene) and its derivatives is reported and it was believed that depolymerization occurred much earlier than the melting transition. We have also demonstrated the orthogonal synthesis of dibenzofulvene monomers using three distinct routes (lithiation, oxidation and Wittig) to cope with functional group compatibility.

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.

Au-catalyzed biaryl coupling to generate 5- to 9-membered rings: Turnover-limiting reductive elimination versus π-complexation

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes-substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to π-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the π-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

Au-Catalyzed Biaryl Coupling to Generate 5- To 9-Membered Rings: Turnover-Limiting Reductive Elimination versus ?-Complexation

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes - substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to ?-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the ?-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

New electron-accepting quinoxalinothiadiazole-containing heterocycles as promising building blocks for organic optoelectronic devices

Two novel quinoxalinothiadiazole-containing dibromides—4,9-dibromo-6,7-bis(9,9-didodecyl7-fluoro-9H-fluoren-2-yl)[1,2,5]thiadiazolo[3,4-g]quinoxaline (11) and 4,9-dibromo-6,7-bis(9,9-didodecyl-5,7-difluoro-9H-fluoren-2-yl)[1,2,5]thiadiazolo[3,4-g]quinoxaline (19)—have been synthesized, which are promising strong electron-accepting building blocks for preparing highly efficient narrow-bandgap D–A conjugated polymers. The composition and structure of monomers 11 and 19 have been proved by elemental analysis data, IR spectroscopy, and 1H and 13C NMR.

Synthesis of new D-A1-D-A2 type low bandgap terpolymers based on different thiadiazoloquinoxaline acceptor units for efficient polymer solar cells

Two low bandgap D-A1-D-A2 conjugated copolymers, namely denoted as P1 (non-fluorine substituted thiadiazoloquinoxaline A2) and P2 (fluorine substituted thiadiazoloquinoxaline A2) with the same D (thiophene) and A1 (benzothiadiazole) groups were synthesize

Efficient palladium-catalyzed C(sp2)-H activation towards the synthesis of fluorenes

A facile protocol for the synthesis of fluorene derivatives has been developed through palladium-catalyzed cyclization of 2′-halo-diarylmethanes via activation of arylic C-H bonds. The reactions occurred smoothly and allowed both electron-rich and electron-deficient substrates to convert into their corresponding fluorenes in good to excellent yields. Studies revealed that this Pd-catalyzed cyclization was also available for the substrates of 2′-chloro-diarylmethanes and no catalyst poisoning occurred for 2′-iodo-diphenylmethane.

Halogen-Adjusted Chemoselective Synthesis of Fluorene Derivatives with Position-Controlled Substituents

Fluorenes have been synthesized through an efficient novel Pd-catalyzed tandem cross-coupling reaction; these substrates are fascinating building blocks found in organic photoelectric materials. The position of the substituent on fluorenes could be conveniently tuned by changing the halogen in the ortho-halobenzyl bromide substrates when coupled with various arylboronic acids. This newly developed synthetic approach could achieve the potential diversity in fluorene-based molecular architectures.