4709-68-6

Usage

Uses

Used in Organic Chemistry:
Benzhydrylidenefluorene is used as a synthetic intermediate for the creation of various organic compounds, leveraging its unique chemical structure to facilitate the development of new molecules with specific functionalities.
Used in Materials Science:
In the field of materials science, benzhydrylidenefluorene is utilized as a component in the production of polymers and advanced materials. Its integration into these materials endows them with particular electronic properties, which are essential for applications in electronic devices and other high-tech industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its role in organic synthesis, benzhydrylidenefluorene could potentially be used in the pharmaceutical industry as a precursor in the development of new drugs, taking advantage of its reactivity and structural features to create bioactive molecules.
Used in Electronic Industry:
Due to its electronic properties, benzhydrylidenefluorene may also find applications in the electronic industry, particularly in the development of materials for semiconductors, sensors, or other electronic components that require specific conductive or resistive properties.
These applications underscore the versatility and importance of benzhydrylidenefluorene in multiple sectors, highlighting its potential to contribute to the advancement of various technologies and products.

InChI:InChI=1/C26H18/c1-3-11-19(12-4-1)25(20-13-5-2-6-14-20)26-23-17-9-7-15-21(23)22-16-8-10-18-24(22)26/h1-18H

Upstream product

• 119-61-9 benzophenone 
• 91805-36-6 fluoren-9-ylmagnesium bromide 
• 86-73-7 9H-fluorene 
• 101-81-5 Diphenylmethane 
• 2051-90-3 Dichlorodiphenylmethane 
• 4709-67-5 9-hydroxy-9-benzhydrylfluorene 
• 75-36-5 acetyl chloride 
• 881-04-9 9H-fluoren-9-yllithium 
• 71-43-2 benzene 
• 104172-71-6 Fluor(2,2,6,6-tetramethylpiperidino)<9-(trimethylsilyl)-9H-fluoren-9-yl>boran 
• 486-25-9 9-fluorenone 
• 132869-70-6 3',3'-diphenyl-spiro[fluoren-9,2'-oxirane] 
• 74-88-4 methyl iodide 
• 632-51-9 1,1,2,2-tetraphenylethylene 

Downstream Products

• 3299-84-1 9-benzoyl-9-phenylfluorene 
• 486-25-9 9-fluorenone 
• 119-61-9 benzophenone 
• 165-09-3 dispiro[9H-fluorene-9,3'-(1,2,4,5-tetroxane)-6',9''-[9H]fluorene] 
• 602-15-3 9,10-diphenylphenanthrene 
• 4425-68-7 9-(diphenylmethyl)fluorene 

Relevant academic research and scientific papers

Reaction of stannenes and phosphastannenes with aldehydes and ketones: New tin four-membered ring derivatives

Stannene Tip2Sn=CR2 1 (Tip = 2,4,6-triisopropylphenyl, CR2 = fluorenylidene) enters a [2+2] cycloaddition reaction with benzophenone to afford the four-membered ring derivative 2. This stannaoxetane undergoes a [2+2] decom

Aggregation-Induced Emission Leading to White Light Emission in Diphenylbenzofulvene Derivatives

The search for a unique molecular system able to efficiently emit in the total visible range of the electromagnetic spectra, i. e., white light emission (WLE), is a topic of intense research. We here show that aggregates formed by diphenylbenzofulvene (DP

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.

Ligand-Free Ru-Catalyzed Direct sp3 C-H Alkylation of Fluorene Using Alcohols

The sp3 C-H alkylation of 9H-fluorene using alcohol and a Ru catalyst via the borrowing hydrogen concept has been described. This reaction was catalyzed by the [Ru(p-cymene)Cl2]2 complex (3 mol %) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to be employed as nonhazardous and greener alkylating agents with the formation of environmentally benign water as a byproduct. A variety of 9H-fluorene underwent selective and exclusive mono-C9-alkylation with primary alcohols in good to excellent isolated yield (26 examples, 50-92% yield), whereas this reaction with secondary alcohols in the absence of any external oxidants furnished the tetrasubstituted alkene as the major product. Furthermore, a base-mediated C-H hydroxylation of the synthesized 9H-fluorene derivatives afforded 9H-hydroxy-functionalized quaternary fluorene derivatives in excellent yield.

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl- 4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at -75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2at -60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. -45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3- dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.

Palladium catalyzed atom-economic synthesis of functionalized 9-(diarylmethylene)-9H-fluorenes using triarylbismuths in one-pot bis-coupling process

An efficient palladium catalyzed atom-economic synthesis of functionalized 9-(diarylmethylene)-9H-fluorenes has been accomplished in one-pot bis-coupling process using triarylbismuths as organometallic reagents. These bis-couplings in 1 hour short reactio

New synthesis of dibenzofulvenes by palladium-catalyzed double cross-coupling reactions

Palladium-catalyzed double cross-coupling reactions of 1,1-bis(pinacolato) borylalk-1-enes with 2,2′-dibromobiaryls and of 9-stannafluorenes with 1,1-dibromoalk-1-enes have been demonstrated to serve as new synthetic methods for dibenzofulvenes.

Copper-catalysed bromoalkynylation of arynes

Arynes were found to be inserted into a C(sp)-Br σ-bond of bromoalkynes in the presence of a copper catalyst, giving (alkynyl)bromoarenes in a straightforward manner.