1836-87-9

Usage

Uses

Used in Chemical Research:
9-Benzylidenefluorene is used as a research compound for studying the properties and behavior of polycyclic aromatic hydrocarbons. Its formation as a by-product in the synthesis of Benz[e]acephenanthrylene makes it a valuable subject for understanding the chemical reactions and mechanisms involved in the synthesis process.
Used in Environmental Studies:
9-Benzylidenefluorene is used as an indicator compound in environmental studies, particularly in the analysis of airborne pollutants, auto exhaust, and tobacco and marijuana smoke. Its presence in these sources can provide insights into the composition and potential health risks associated with exposure to these pollutants.
Used in Analytical Chemistry:
9-Benzylidenefluorene can be employed as a reference compound in analytical chemistry for the development and validation of methods and techniques for the detection and quantification of polycyclic aromatic hydrocarbons in various samples, including environmental and biological matrices.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 9-Benzylidenefluorene may have potential applications in the pharmaceutical industry as a starting material or intermediate for the synthesis of more complex molecules with potential therapeutic properties. Further research and development would be required to explore these possibilities.

InChI:InChI=1/C22H16/c1-2-9-17(10-3-1)11-8-16-22-20-14-6-4-12-18(20)19-13-5-7-15-21(19)22/h1-16H/b11-8+

Upstream product

• 86-73-7 9H-fluorene 
• 141-52-6 sodium ethanolate 
• 100-52-7 benzaldehyde 
• 63839-89-4 Acetoxy-(9-fluorenyl)-phenyl-methan 
• 7351-45-3 9,9'-bis(trimethylsilyl)fluorene 
• 7385-10-6 9-(trimethylsilyl)fluorene 
• 10271-61-1 2-iodo-2'-(phenylethynyl)biphenyl 
• 56954-91-7 (9H-fluoren-9-yl)(phenyl)methanol 
• 7647-01-0 hydrogenchloride 
• 36322-03-9 9-benzyl-9-fluorenol 
• 64-19-7 acetic acid 
• 591-50-4 iodobenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 4709-64-2 9,9-bis(benzyl)fluorene 
• 16573-51-6 6-benzyl-phenanthridine 
• 1572-46-9 9-benzylfluorene 
• 4425-68-7 9-(diphenylmethyl)fluorene 
• 79898-41-2 9-bromo-9-[bromo-(phenyl)methyl]-9H-fluorene 
• 142532-71-6 9,9'-dibenzyl-[9,9']bifluorenyl 
• 80310-51-6 C₃₁H₁₉NO₂ 
• 80310-38-9 C₄₂H₃₂N₂O₄ 
• 80310-37-8 C₄₀H₂₆N₄O₈ 
• 5455-02-7 9-<(4-methoxyphenyl)imino>fluorene 
• 79918-27-7 (4-Methoxy-phenyl)-(10-phenyl-phenanthren-9-yl)-amine 
• 19656-47-4 fluoren-9-ylidene-phenyl-acetonitrile 
• 19656-51-0 9-(α-Cyan-benzyl>-fluoren 
• 1572-47-0 9-(3-Carbaethoxy-1-phenylpropyl)fluoren 

Relevant academic research and scientific papers

Synthesis of 9-alkylidene-9H-fluorenes by a novel, palladium-catalyzed cascade reaction of aryl halides and 1-aryl-1-alkynes

In the presence of a palladium catalyst and NaOAc, aryl iodides react with 1-aryl-1-alkynes to afford 9-alkylidene-9H-fluorenes in good yields. The products from this reaction are highly dependent on the base employed. This process appears to involve (1)

Design and synthesis of extended π-systems: Monomers, oligomers, polymers

The synthesis of unconventional extended π-systems is described in an attempt to tailor the structures of organic compounds for specific optical and electrical properties. In order to emphasize the role of the π-conjugation and to correlate chemical structure and physical function both one-dimensional arylenevinylenes and two-dimensional ribbon-type molecules are considered. In the synthesis of the former the aryl-olefin coupling according to Heck is of special value, the synthesis of the latter is achieved by repetitive Diels-Alder cycloadditions and by two-step processes in which carefully designed polyaryl precursors are subjected to ring closure. Key ingredients of the present approach are the interplay of synthetic organic chemistry and synthetic macromolecular chemistry and the needs outlined by materials sciences. Thereby, transition from monomers to oligomers and polymers defines new requirements for the selectivity of the synthetic reactions and the tractability of the products.

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

An N-heterocyclic carbene-catalyzed switchable reaction of 9-(trimethylsilyl)fluorene and aldehydes: Chemoselective synthesis of dibenzofulvenes and fluorenyl alcohols

An N-heterocyclic carbene-catalyzed synthesis of dibenzofulvenes and fluorenyl alcohols was developed. In the presence of 10 mol% NHC (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) and 4 ? molecular sieves, 9-(trimethylsilyl)fluorene undergoes an olef

Manganese catalyzed switchableC-alkylation/alkenylation of fluorenes and indene with alcohols

The usage of earth-abundant, nontoxic transition metals in place of rare noble metals is a central goal in catalysis. This would be especially interesting when the reactivity and selectivity patterns can be tuned. Herein, we introduced the first Mn-catalyzed selectiveC-alkylation and olefination of fluorene, and indene with alcohols. Various substrates including benzylic, heteroaromatic, and aliphatic primary and secondary alcohols are employed as alkylating agents. Mechanistic investigations and a kinetic study underpin the involvement of the olefinated intermediate to furnish the alkylated product.

Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes

An atom economical protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. The reaction proceeds through the C-H activation/oxidative addition/reduction elimination/intramolecular Heck coupling reaction to afford a series of 9-(diorganomethylidene)fluorenes with good yields. Control experiments demonstrate that a five-membered palladacycle acts as a key intermediate and β-H elimination serves as the rate-limiting step.

Synthesis of 9-Fluorenylidenes via Pd-Catalyzed C-H Vinylation with Vinyl Bromides

A facile and efficient approach for the synthesis of 9-fluorenylidenes has been developed via the palladium-catalyzed cross-coupling of 2-iodobiphenyls and vinyl bromides. The reaction involves the C-H activation of 2-iodobiphenyls and dual C-C bond formations. A range of 9-fluorenylidene derivatives, including diphenyldibenzofulvenes, can be synthesized with the reaction.

α-Bromoacrylic Acids as C1 Insertion Units for Palladium-Catalyzed Decarboxylative Synthesis of Diverse Dibenzofulvenes

Herein α-bromoacrylic acids have been employed as C1 insertion units to achieve the palladium-catalyzed [4 + 1] annulation of 2-iodobiphenyls, which provides an efficient platform for the construction of diverse dibenzofulvenes. This protocol enables the formation of double C(aryl)-C(vinyl) bonds via a C(vinyl)-Br bond cleavage and decarboxylation. It is particularly noteworthy that the method features a broad substrate scope, and various interesting frameworks, such as bridged ring, fused (hetero)aromatic ring, and divinylbenzene, can be successfully incorporated into the products.

Manganese-Catalyzed Synthesis of Quaternary Peroxides: Application in Catalytic Deperoxidation and Rearrangement Reactions

Highly efficient, selective, and direct C-H peroxidation of 9-substituted fluorenes has been achieved using a Mn-2,2′-bipyridine catalyst via radical-radical cross-coupling. Moreover, this method effectively promotes the vicinal bisperoxidation of sterically hindered various substituted arylidene-9H-fluorene/arylideneindolin-2-one derivatives to afford highly substituted bisperoxides with high selectivity over the oxidative cleavage of Ca C bond that usually forms the ketone of an aldehyde. Furthermore, a new approach for the synthesis of (Z)-6-benzylidene-6H-benzo[c]chromene has been achieved via an acid-catalyzed skeletal rearrangement of these peroxides. For the first time, unlike O-O bond cleavage, reductive C-O bond cleavage in peroxides using the Pd catalyst and H2 is described, which enables the reversible reaction to afford exclusively deperoxidized products. A detailed mechanism for peroxidation, molecular rearrangement, and deperoxidation has been proposed with preliminary experimental evidences.

Intermolecular oxidative Friedel-Crafts reaction triggered ring expansion affording 9,10-diarylphenanthrenes

A novel intermolecular tandem oxidative aromatic coupling between arylidene fluorenes and unfunctionalized aromatics mediated by a DDQ/TFA oxidation system has been developed for the construction of 9,10-diary-lphenanthrenes (DAPs). The formation of a benzylic carbocation species possessing a quaternary sp3-carbon center on the fluorene moiety by an intermolecular oxidative Friedel-Crafts reaction of two different arenes successfully triggered the subsequent ring expansion to afford DAPs.