440-40-4

Usage

Uses

Used in Pharmaceutical Research and Development:
3-Fluorophenanthrene is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique reactivity and properties make it a valuable building block for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
3-Fluorophenanthrene is used as a starting material in the synthesis of various organic compounds. Its fluorinated nature allows for the formation of new chemical bonds and reactions that are not possible with non-fluorinated compounds, expanding the scope of organic synthesis.
Used in Material Science:
3-Fluorophenanthrene has potential applications in the development of new materials with unique properties. Its incorporation into polymers, coatings, and other materials can lead to improved performance and functionality.
It is important to handle 3-Fluorophenanthrene with caution, as it may pose health and safety risks if not properly managed.

Upstream product

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• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 159957-00-3 1-(2,2-dibromovinyl)-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 870122-74-0 2-bromo-1-(4-fluorophenyl)ethylene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 405-99-2 para-fluorostyrene 
• 4120-78-9 N-(phenanthren-3-yl)acetamide 
• 718-25-2 (E)-4-fluorostilbene 
• 15160-73-3 C₁₄H₁₀BrF 

Relevant academic research and scientific papers

Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst

Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Br?nsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Oxidative, Iodoarene-Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons

A catalytic, metal-free and chemoselective oxidative intramolecular coupling of arene and alkene C?H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta-chloroperoxybenzoic acid (m-CPBA), reacts with o-vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium and, possibly, vinylenephenonium intermediates.

Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.

Air-Driven Potassium Iodide-Mediated Oxidative Photocyclization of Stilbene Derivatives

A new method has been developed for the potassium iodide-mediated oxidative photocyclization of stilbene derivatives. Compared with conventional iodine-mediated oxidative photocyclization reactions, this new method requires shorter reaction times and affords cyclized products in yields of 45-97%. This reaction proceeds with a catalytic amount of potassium iodide and works in an air-driven manner without the addition of an external scavenger. The radical-mediated oxidative photocyclization of stilbene derivatives using TEMPO was also investigated.

A combined experimental and computational study on the cycloisomerization of 2-ethynylbiaryls catalyzed by dicationic arene ruthenium complexes

Ruthenium-catalyzed cycloisomerization of 2-ethynylbiaryls was investigated to identify an optimal ruthenium catalyst system. A combination of [η6-(p-cymene)RuCl2(PR3)] and two equivalents of AgPF6 effectively converted 2-ethynylbiphenyls into phenanthrenes in chlorobenzene at 120 °C over 20 h. Moreover, 2-ethynylheterobiaryls were found to be favorable substrates for this ruthenium catalysis, thus achieving the cycloisomerization of previously unused heterocyclic substrates. Moreover, several control experiments and DFT calculations of model complexes were performed to propose a plausible reaction mechanism.

Expeditious synthesis of fluorinated styrylbenzenes and polyaromatic hydrocarbons

A series of fluorinated styrylbenzene derivatives were synthesized by the Mizoroki-Heck reaction using phosphine-free catalytic conditions or by adopting the one-pot Wittig-Heck reaction sequence. The fluorinated styrylbenzenes were converted into polyaromatic hydrocarbons such as phenanthrenes, [4]helicenes, and benzo[ghi]perylene by a modified photocyclization procedure involving I 2-THF condition.

Straightforward synthesis of phenanthrenes from styrenes and arenes

Semi-one-pot synthesis of phenanthrenes from styrenes and arenes was developed through cross-dehydrogenative coupling. A sequence of Heck-type coupling and photo-cyclization were involved and a variety of functionalities were tolerated. This method provides an effective and practical protocol towards the synthesis of substituted phenanthrenes. The Royal Society of Chemistry 2012.