523-41-1

Usage

Uses

Used in Pharmaceutical Development:
2-Fluorophenanthrene is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs due to its unique chemical properties.
Used in Agrochemical Production:
In the agrochemical industry, 2-Fluorophenanthrene is utilized as a precursor in the creation of novel agrochemicals, potentially enhancing crop protection and yield.
Used in Materials Science:
2-Fluorophenanthrene plays a role in materials science, where it is employed in the synthesis of advanced materials with specific properties, such as those used in electronic devices or specialty coatings.

InChI:InChI=1/C14H9F/c15-12-7-8-14-11(9-12)6-5-10-3-1-2-4-13(10)14/h1-9H

Upstream product

• 261713-83-1 1-bromo-2-[2-[tris(1-methylethyl)silyl]ethynyl]benzene 
• 1374249-51-0 (2-{[tris(1-methylethyl)silyl]ethynyl}phenyl)boronic acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 78602-28-5 1-bromo-2-(2-phenylethenyl)benzene 
• 130089-19-9 1-bromo-2-(2-methoxyethenyl)benzene 
• 96557-30-1 2-bromophenylacetaldehyde 
• 1392144-15-8 C₂₈H₂₅FN₄O₄S₂ 
• 343-43-1 2-fluoro-9H-fluorene 
• 19466-30-9 (E)-3-fluorostilbene 
• 3937-78-8 (2-fluoro-fluoren-9-yl)-methanol 

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.

Alumina-Mediated π-Activation of Alkynes

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

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.

Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Br?nsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol

The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Br?nsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.

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.

Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds

Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright

Palladium-catalyzed intramolecular C-H activation: A synthetic approach towards polycyclic aromatic hydrocarbons

A simple and convenient synthetic protocol for the construction of polycyclic aromatic hydrocarbons has been developed. A variety of phenanthrene, benzo[c]phenanthrene and chrysene derivatives was synthesized via Pd-catalyzed intramolecular C-H activation followed by acid-catalyzed water elimination.