30203-84-0

Usage

Uses

Used in Organic Synthesis:
1-(4-Bromobenzyl)-4-chlorobenzene is used as a versatile intermediate for the production of a wide range of organic compounds. Its ability to react with various reagents allows for the formation of other functionalized benzene derivatives, which are essential in creating new materials and chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(4-Bromobenzyl)-4-chlorobenzene is used as a building block in the design and synthesis of potential drug candidates. Its unique structure and reactivity contribute to the development of new pharmaceuticals with specific therapeutic properties.
Used in Agrochemicals:
BCB also plays a role in the agrochemical industry, where it is utilized in the development of new compounds with applications in agriculture, such as pesticides and herbicides.
Used in the Development of New Materials:
The structure and reactivity of 1-(4-Bromobenzyl)-4-chlorobenzene make it an important reagent in the creation of new materials with potential applications in various industries, including electronics, coatings, and plastics.

InChI:InChI=1/C13H10BrCl/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9H2

Upstream product

• 107071-33-0 1-(p-bromobenzyl)-2-t-butyl-4-(p-fluorophenyl)-6-phenylpyridinium trifluoromethanesulphonate 
• 108-90-7 chlorobenzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 115055-85-1 bromo-[(4-bromophenyl)methyl]zinc 
• 1679-18-1 4-Chlorophenylboronic acid 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 873-75-6 4-bromobenzenemethanol 
• 104-88-1 4-chlorobenzaldehyde 
• 106-37-6 1.4-dibromobenzene 
• 108-86-1 bromobenzene 
• 873-76-7 para-Chlorobenzyl alcohol 
• 1352918-92-3 N-((4-chlorobenzyl)oxy)-N-methylacetamide 
• 4450-67-3 4-chlorobenzyl 4-methylbenzenesulfonate 
• 105901-10-8 1-((4-bromophenyl)-(4-chlorophenyl))methanol 

Downstream Products

• 27428-57-5 4-bromo-4'-chlorobenzophenone 
• 30203-87-3 1-chloro-4-(4-methylbenzyl)benzene 
• 17100-53-7 1-bromo-4-(4-methylbenzyl)benzene 

Relevant academic research and scientific papers

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel-Crafts reactions

This manuscript describes the application of Re2O7 to the syntheses of diarylmethanes from benzylic alcohols through solvolysis followed by Friedel-Crafts alkylation. The reactions are characterized by broad substrate scope, low catalyst loadings, high chemical yields, and minimal waste generation. The intermediate perrhenate esters are superior leaving groups to chlorides and bromides in these reactions. The polarity and water sequestering capacity of hexafluoroisopropyl alcohol are critical to the success of these processes. Re2O7 is a precatalyst for HOReO3, which serves as a less costly and easily handled promoter for these reactions. Oxorhenium catalysts selectively activate alcohols in the presence of similarly substituted acetates, indicating a unique chemoselectivity and mechanism in comparison to Br?nsted acid catalysis.

Investigating the Reactivity of 1,4-Anthracene-Incorporated Cycloparaphenylene

Cycloparaphenylenes (CPPs) and their derivatives are unique conjugated macrocycles with novel optoelectronic and host-guest properties. A better understanding of their reactivity is essential for creating new functional materials utilizing these strained

Unsymmetrical diarylmethanes by ferroceniumboronic acid catalyzed direct friedel-crafts reactions with deactivated benzylic alcohols: Enhanced reactivity due to ion-pairing effects

The development of general and more atom-economical catalytic processes for Friedel-Crafts alkylations of unactivated arenes is an important objective of interest for the production of pharmaceuticals and commodity chemicals. Ferroceniumboronic acid hexafluoroantimonate salt (1) was identified as a superior air- and moisture-tolerant catalyst for direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes with stable and readily available primary and secondary benzylic alcohols. Compared to the use of classical metal-catalyzed alkylations with toxic benzylic halides, this methodology employs exceptionally mild conditions to provide a wide variety of unsymmetrical diarylmethanes and other 1,1-diarylalkane products in high yield with good to high regioselectivity. The optimal method, using the bench-stable ferroceniumboronic acid salt 1 in hexafluoroisopropanol as cosolvent, displays a broader scope compared to previously reported catalysts for similar Friedel-Crafts reactions of benzylic alcohols, including other boronic acids such as 2,3,4,5-tetrafluorophenylboronic acid. The efficacy of the new boronic acid catalyst was confirmed by its ability to activate primary benzylic alcohols functionalized with destabilizing electron-withdrawing groups like halides, carboxyesters, and nitro substituents. Arene benzylation was demonstrated on a gram scale at up to 1 M concentration with catalyst recovery. Mechanistic studies point toward the importance of the ionic nature of the catalyst and suggest that factors other than the Lewis acidity (pKa) of the boronic acid are at play. A SN1 mechanism is proposed where ion exchange within the initial boronate anion affords a more reactive carbocation paired with the non-nucleophilic hexafluoroantimonate counteranion.

Flow chemistry as a discovery tool to access sp2-sp3 cross-coupling reactions via diazo compounds

The work takes advantage of an important feature of flow chemistry, whereby the generation of a transient species (or reactive intermediate) can be followed by a transfer step into another chemical environment, before the intermediate is reacted with a coupling partner. This concept is successfully applied to achieve a room temperature sp2-sp3 cross coupling of boronic acids with diazo compounds, these latter species being generated from hydrazones under flow conditions using MnO2 as the oxidant.

Highly efficient method for solvent-free synthesis of diarylmethane and triarylmethane from benzylic alcohols using P2O5/Al 2O3 or P2O5/SiO2 at room temperature

A highly efficient procedure for the synthesis of triarylmethane and diarylmethane via benzylation of aromatic hydrocarbons from benzyl alcohols using supported P2O5 on SiO2 and/or Al 2O3 under solvent-free conditions is described. Excellent yields of triarylmethane and diarylmethane were obtained using P 2O5-SiO2 (50%W/W) and/or P2O 5-Al2O3 (50%W/W) at room temperature. The reusability of both supported P2O5 on SiO2 and Al2O3 were examined. Both supported reagents show favorable activities in first and second runs, however, a decline in reactivity was observed in following attempts. The reaction is scalable to > 0.03 mole amounts.

Friedel-crafts benzylation of activated and deactivated arenes

NO going back makes possible facile Friedel-Crafts benzylations with moderate reaction temperatures, simple reaction workups, and improved substrate scope for the formation of synthetically important diarylmethanes (see scheme). Upon complexation with BF3?OEt2, hydroxamates serve as reversible leaving groups that stabilize highly reactive carbocations. Even deactivated arenes and electron-deficient benzylhydroxamates react cleanly under these conditions.

New multi-coupling benzylic zinc reagents for the preparation of flexible aromatic compounds

The benzylic zinc reagents 3a-c bearing a triflate group in o-, m- or p-position are new efficient multi-coupling reagents reacting stepwise with an aryl iodide (Ar1-I) and an arylzinc bromide (Ar2ZnBr) in the presence of the appropriate palladium catalyst and the suitable phosphine ligand leading to polyfunctional flexible aromatic products of type 5. This methodology is appropriate for applications in combinatorial chemistry.

Identification of the Products of Solvolysis of N-Benzylpyridinium Cations in the Absence of Nucleophiles

Mono-, tri-, and penta-cyclic N-benzylpyridinium tetrafluoroborates undergo tharmolysis in chlorobenzene as solvent to give products of benzylation both of the solvent and of the pyridine leaving group.Thermolysis alone, and in nitrobenzene as solvent, yielded mainly products of benzylation of the leaving group.The results support the previously postulated mechanism of unimolecular solvolysis of compounds of these types in non-polar solvents.