37503-79-0

Usage

Uses

Used in Materials Science:
(Sp)-4-bromo[2.2]paracyclophane is used as a component in the development of new materials due to its unique structural and chemical properties.
Used in Organic Synthesis:
(Sp)-4-bromo[2.2]paracyclophane is used as a reactant in organic synthesis for the creation of various complex organic molecules, taking advantage of its reactivity and structural features.
Used in Pharmaceutical Industry:
(Sp)-4-bromo[2.2]paracyclophane is used as a chiral building block for the synthesis of pharmaceuticals, leveraging its chiral nature to create enantiomerically pure drugs.
Used in Agrochemicals:
(Sp)-4-bromo[2.2]paracyclophane is used as a chiral building block in the development of agrochemicals, such as pesticides and fertilizers, to enhance their effectiveness and selectivity.
Used in Asymmetric Synthesis:
(Sp)-4-bromo[2.2]paracyclophane is used as a chiral auxiliary or catalyst in asymmetric synthesis to produce enantiomerically enriched products.
Used in Chromatography:
(Sp)-4-bromo[2.2]paracyclophane is used as a chiral selector in chromatography for the separation of enantiomers, taking advantage of its ability to interact differently with each enantiomer.

Upstream product

• 1633-22-3 [2.2]Paracyclophan 
• 1908-61-8 4-bromo[2.2]paracyclophane 
• 7726-95-6 bromine 
• 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 
• 10122-95-9 (R_p)-1,4(1,4)-dibenzenacyclohexaphan-1²-amine 

Downstream Products

• 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 
• 160727-05-9 4-(4’-tolyl)[2.2]paracyclophane 
• 162103-13-1 4-(4-methoxyphenyl)-<2.2>paracyclophane 
• 5628-14-8 4-Hydroxy-7-benzolazo<2.2>paracyclophan 

Relevant academic research and scientific papers

Planar chirality change in dediazoniation reactions of paracyclophanes and mechanistic implication

Dediazoniation reactions of (Sp)-4-bromo-13-[2.2] paracyclophanyldiazonium fluoborate 2a through a heterolytic cleavage process gave products with partial racemization. In contrast, dediazoniation reactions of (Sp)-2a undergoing a nonheterolytic cleavage process afforded products with retention of configuration. A key intermediate, the bromonium cation B, caused the racemization. The unexpected racemization allowed the mechanisms of the dediazoniation reaction to be probed.

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).

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.

[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.

Immobilization of catalysts in poly(p-xylylene) nanotubes

This paper describes the immobilization of a TEMPO-derivative and a copper catalyst in ethinyl-functionalized poly(p-xylylene) nanotubes which are readily prepared by the Tubes by Fiber Templates (TUFT) process. Catalyst conjugation to the nanotubes is achieved via the Cu-catalyzed azide alkyne cycloaddition (CuAAC). The TEMPO-functionalized nanotubes are successfully used as recyclable catalysts for oxidation of benzyl alcohol. Recycling studies show that the TEMPO-modified nanotubes can be reused 20 times without loss of catalytic activity. Conjugation of the nanotubes with a bipyridine moiety provides a material that allows for immobilization of metal catalysts. Treatment with a Cu(i)-salt leads to a hybrid material, which shows high activity as a recyclable catalyst in the CuAAC. Recycling experiments reveal that these Cu-nanotubes can be reused for 18 runs.