1908-61-8

Usage

Uses

Used in Materials Science:
4-BROMO[2.2]PARACYCLOPHANE is used as a building block for the development of novel materials due to its unique structure and properties, which can contribute to the creation of advanced materials with specific characteristics for various applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-BROMO[2.2]PARACYCLOPHANE serves as a key intermediate or reactant in the synthesis of complex organic molecules, taking advantage of its reactive sites and structural features to form new compounds with desired properties.
Used in Molecular Recognition:
4-BROMO[2.2]PARACYCLOPHANE is utilized in molecular recognition processes, where its unique structure allows for selective binding and interactions with specific target molecules, which is crucial in areas such as chemical sensing, diagnostics, and drug design.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 4-BROMO[2.2]PARACYCLOPHANE is used as a potential candidate for drug discovery and development, given its unique properties that may contribute to the design of new therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Development:
4-BROMO[2.2]PARACYCLOPHANE is also considered in the agrochemical sector for the development of new pesticides or herbicides, leveraging its chemical properties to target specific pests or weeds while minimizing environmental impact.

InChI:InChI=1/C16H15Br/c17-16-11-14-6-5-12-1-3-13(4-2-12)7-9-15(16)10-8-14/h1-4,8,10-11H,5-7,9H2

Upstream product

• 1633-22-3 [2.2]Paracyclophan 
• 735-65-9 2-bromo-1-tricyclo[8.2.2.24,7]hexadeca-1⁽¹³⁾,4,6,10⁽¹⁴⁾,11,15-hexaen-5-yl-ethanone 
• 7726-95-6 bromine 

Downstream Products

• 98395-17-6 4-styryl[2.2]paracyclophane 
• 88787-15-9 4-phenyl-<2.2>paracyclophane 
• 135562-22-0 (-)-(R_P,S_S)-4-(p-toluenesulfinyl)<2.2>paracyclophane 
• 135562-22-0 (+)-(S_P,S_S)-4-(p-toluenesulfinyl)<2.2>paracyclophane 
• 1633-22-3 [2.2]Paracyclophan 
• 5628-11-5 4-hydroxy-[2,2]-paracyclophane 
• 162103-13-1 4-(4-methoxyphenyl)-<2.2>paracyclophane 
• 160727-05-9 4-(4’-tolyl)[2.2]paracyclophane 
• 5551-40-6 5-Hydroxy-4-methylmercypto-<2,2>paracyclophan 
• 18931-44-7 pseudo-p-Brom-acetyl-<2,2>paracyclophan 
• 511254-84-5 1-benzyl-4-[2.2]paracyclophan-4-ylpiperazine 
• 880517-49-7 α-pyridyl([2.2]paracyclophan-4-yl)phenylmethanol 

Relevant academic research and scientific papers

Layered Compounds. LXIII. Bromination of Double- and Triple-layered Paracyclophanes

Triple-layered paracyclophanes underwent bromination to give exclusively monobromo derivatives substituted to the inner benzene.The reactions were markedly accelerated by the transannular electronic interaction as compared to - and double-layered paracyclophanes, and thier enhanced reactivities were demonstrated by some competitive reactions.The relative rates of and systems are in reverse order for the triple-layered and double-layered series.Their reaction mechanisms were discussed.

Enantiospecific synthesis of [2.2]paracyclophane-4-thiol and derivatives

This paper describes a simple route to enantiomerically enriched [2.2]paracyclophane-4-thiol via the stereospecific introduction of a chiral sulfoxide to the [2.2]paracyclophane skeleton. The first synthesis of an enantiomerically enriched planar chiral benzothiazole is also reported.

Homochiral [2.2]Paracyclophane Self-Assembly Promoted by Transannular Hydrogen Bonding

[2.2]paracyclophane (pCp), unlike many π-building blocks, has been virtually unexplored in supramolecular constructs. Reported here is the synthesis and characterization of the first pCp derivatives capable of programmed self-assembly into extended cofacial π-stacks in solution and the solid state. The design employs transannular (intramolecular) hydrogen bonds (H-bonds), hitherto unstudied in pCps, between pseudo-ortho-positioned amides of a pCp-4,7,12,15-tetracarboxamide (pCpTA) to preorganize the molecules for intermolecular H-bonding with π-stacked neighbors. X-ray crystallography confirms the formation of homochiral, one-dimensional pCpTA stacks helically laced with two H-bond strands. The chiral sense is dictated by the planar chirality (Rpor Sp) of the pCpTA monomers. A combination of NMR, IR, and UV/Vis studies confirms the formation of the first supramolecular pCp polymers in solution.

Development of Planar Chiral Iodoarenes Based on [2.2]Paracyclophane and Their Application in Catalytic Enantioselective Fluorination of β-Ketoesters

The design and synthesis of novel planar chiral iodoarenes based on [2.2]paracyclophane is reported. A process of highly enantioselective oxidative fluorination of a β-ketoester with 3HF-Et3N as a nucleophilic fluoride source mediated by these new hypervalent iodine catalysts has been developed. This represents the first highly enantioselective reaction catalyzed by planar chiral hypervalent iodine.

Planar-Chiral [2.2]Paracyclophane-Based Amides as Proligands for Titanium- and Zirconium-Catalyzed Hydroamination

A synthetic route to racemic and enantiopure planar chiral [2.2]paracyclophanes with amide groups was developed to combine the well-established reactivity of amides as N,O-chelating ligands in hydroamination reactions with the planar chirality of the [2.2

[2.2]Paracyclophanes with N-Heterocycles as Ligands for Mono- and Dinuclear Ruthenium(II) Complexes

[2.2]Paracyclophane, with its unique structure, allows the design of unusual 3D structures by functionalization of this rigid and stable hydrocarbon scaffold. Therefore different mono- and homodisubstituted [2.2]paracyclophanes with pyridyl, pyrimidyl and oxazolinyl substituents were developed in order to evaluate their ability as bridging ligands for two ruthenium centres. With the successfully synthesized [2.2]paracyclophane-based N-donor functions, the cycloruthenation reaction using [RuCl2(p-cymene)]2 as precursor was explored. Compared to 2-phenylpyridine, the [2.2]paracyclophane derivative is clearly inferior in the cycloruthenation reaction, resulting in poor yields for the neutral complexes. By addition of KPF6, the cationic complexes can be obtained in good yields and are formed diastereoselectively in case of a pyridyl substituent, resulting in only one diastereomer for dinuclear ruthenium complexes of bispyridyl-substituted [2.2]paracyclophanes as bridging ligands.

Unprecedented One-Pot Reaction towards Chiral, Non-Racemic Copper(I) Complexes of [2.2]Paracyclophane-Based P,N-Ligands

Herein, we report a simple one-pot route to enantiopure copper(I) complexes featuring a unique [2.2]paracyclophane-based P,N-ligand system. Phosphine and pyridine moieties can be varied allowing the modular synthesis of these rigid and stable [2.2]paracyclophane-based P,N-ligands. These P,N-ligands are a new ligand class for different transition-metal complexes, which is shown exemplarily for palladium(II).

[2-2]PARACYCLOPHANE-DERIVED DONOR/ACCEPTOR-TYPE MOLECULES FOR OLED APPLICATIONS

Disclosed are [2.2]paracyclophane-derivative compounds and related polymers that are useful as stable, efficient, blue-light emitting compounds for OLED applications.

Chiral [2.2]paracyclophane-based NAC- and NHC-gold(I) complexes Dedicated to Prof. Hubert Schmidbaur on the occasion of his 80th birthday.

From enantiomerically pure, planar chiral [2.2]paracyclophane amines a series of nitrogen acyclic carbenegold(I) complexes and nitrogen heterocyclic carbenegold(I) complexes are prepared by a modular template synthesis using isonitriles and amines. These

Metal-free catalytic hydrogenation of imines with recyclable [2.2]paracyclophane-derived frustrated lewis pairs catalysts

A series of [2.2]paracyclophane-derived frustrated Lewis pairs (FLPs) with reversible, metal-free hydrogen activation was synthesized and successfully applied in the hydrogenation of imines in moderate to good yields. The high stability of the novel FLP system enables effective recycling of the metal-free catalysts. This reaction could also be compatible with a larger scale and developed into a pharmaceutical synthesis of cinacalcet {(R)-N-[1-(1-naphthyl) ethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine} without heavy metal residues.