17100-53-7

Usage

Uses

Used in Organic Synthesis:
Benzene, 1-bromo-4-[(4-methylphenyl)methyl]is used as an intermediate in organic synthesis for the production of various compounds. Its unique structure allows for further chemical reactions and modifications, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Benzene, 1-bromo-4-[(4-methylphenyl)methyl]is used as a key intermediate in the development of new drugs and pharmaceutical compounds. Its versatile structure enables the creation of novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
Benzene, 1-bromo-4-[(4-methylphenyl)methyl]is also utilized in chemical research to study the properties and reactions of aromatic compounds. Its unique structure provides insights into the behavior of bromine-substituted aromatics and their interactions with other chemical entities.
Used in Material Science:
In material science, Benzene, 1-bromo-4-[(4-methylphenyl)methyl]can be used as a precursor for the development of new materials with specific properties. Its aromatic structure and bromine atom can contribute to the formation of materials with unique electronic, optical, or mechanical characteristics.

Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 5142-75-6 tri(p-tolyl)bismuth 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 589-17-3 p-bromobenzyl chloride 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 873-75-6 4-bromobenzenemethanol 
• 108-88-3 toluene 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 
• 1122-91-4 4-bromo-benzaldehyde 
• 5467-74-3 4-Bromophenylboronic acid 
• 104-81-4 4-Methylbenzyl bromide 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 76693-57-7 (4-bromophenyl)(p-tolyl)methanone 

Relevant academic research and scientific papers

Multi-component one-pot reaction of aromatic carbonyl compounds, tosylhydrazide, and arylboronic acids

In this paper, we developed a new method using 4-bromoacetophenone as the starting material, with tosylhydrazide and two arylboronic acids using Barluenga and Suzuki couplings in a four-component one-pot reaction to afford the target product 4-benzyl-1,1-biphenyls. This system that we have developed enables the use of easily accessible starting materials and can be employed on a wide variety of substrates with good functional group tolerance. In particular, this protocol can be applied to the synthesis of 4-(1-([1,1-biphenyl]-4-yl)ethyl)pyridine derivatives, a class of potential analogs of CPY17 inhibitors of prostate cancer.

Cooperative Al-H Bond Activation in DIBAL-H: Catalytic Generation of an Alumenium-Ion-Like Lewis Acid for Hydrodefluorinative Friedel-Crafts Alkylation

The Ru-S bond in Ohki-Tatsumi complexes breaks oligomeric DIBAL-H structures into their more reactive monomer. That deaggregation is coupled to heterolytic Al-H bond activation at the Ru-S bond, formally splitting the Al-H linkage into hydride and an alumenium ion. The molecular structure of these Lewis pairs was established crystallographically, revealing an additional Ru-Al interaction next to the Ru-H and Al-S bonds. That bonding situation was further analyzed by quantum-chemical calculations and is best described as a three-center-two-electron (3c2e) donor-acceptor σ(Ru-H) → Al interaction. Despite the extra stabilization of the aluminum center by the interaction with both the sulfur atom and the Ru-H bond, the hydroalane adducts are found to be stronger Lewis acids and electrophiles than the free ruthenium catalyst and DIBAL-H in its different aggregation states. Hence, the DIBAL-H molecule and its Al-H bond are activated by the Ru-S bond, but these hydroalane adducts are not to be mistaken as sulfur-stabilized alumenium ions in a strict sense. The Ohki-Tatsumi complexes catalyze C(sp3)-F bond cleavage with DIBAL-H, and the catalytic setup is applied to hydrodefluorinative Friedel-Crafts alkylations. A broad range of CF3-substituted arenes is efficiently converted into unsymmetrical diarylmethanes with various arenes as nucleophiles. Computed fluoride-ion affinities (FIAs) of the hydroalane adducts as well as DIBAL-H in its aggregation states support this experimental finding.

Synthetic method of diarylmethanes

The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.

Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts

We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.

Benzylic Phosphates in Friedel-Crafts Reactions with Activated and Unactivated Arenes: Access to Polyarylated Alkanes

Easily reachable electron-poor/rich primary and secondary benzylic phosphates are suitably used as substrates for Friedel-Crafts benzylation reactions with only 1.2 equiv activated/deactivated arenes (no additional solvent) to access structurally and electronically diverse polyarylated alkanes with excellent yields and selectivities at room temperature. Specifically, diversely substituted di/triarylmethanes are generated within 2-30 min using this approach. A wide number of electron-poor polyarylated alkanes are easily accomplished through this route by just tuning the phosphates.

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.

Threefold and chemoselective couplings of triarylbismuths with benzylic chlorides and iodides using palladium catalysis

This paper describes the palladium-catalyzed studies on threefold coupling of triarylbismuth reagents with benzylic chlorides and iodides. The optimized protocol conditions are operationally simple, delivering threefold coupling of a variety of triarylbismuths in combination with benzylic chlorides and iodides. The two optimized protocols allowed the synthesis of a diverse range of unsymmetrical diarylmethanes in an efficient manner. As part of this study, chemoselective transformation of benzylic chlorides and iodides was also achieved. This journal is the Partner Organisations 2014.

Iron phosphine catalyzed cross-coupling of tetraorganoborates and related group 13 nucleophiles with alkyl halides

Iron phosphine complexes prove to be good precatalysts for the cross-coupling of alkyl, benzyl, and allyl halides with not only aryl triorganoborate salts but also related aluminum-, gallium-, indium-, and thallium-based nucleophiles. Mechanistic studies revealed that while Fe(I) can be accessed on catalytically relevant time scales, lower average oxidation states are not formed fast enough to be relevant to catalysis. EPR spectroscopic studies reveal the presence of bis(diphosphine)iron(I) complexes in representative catalytic reactions and related processes with a range of group 13 nucleophiles. Isolated examples were studied by M?ssbauer spectroscopy and single-crystal X-ray structural analysis, while the electronic structure was probed by dispersion-corrected B3LYP DFT calculations. An EPR study on an iron system with a bulky diphosphine ligand revealed the presence of an S = 1/2 species consistent with the formation of a mono(diphosphine)iron(I) species with inequivalent phosphine donor environments. DFT analysis of model complexes allowed us to rule out a T-shaped Fe(I) structure, as this is predicted to be high spin.

Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3-H2O

An efficient and environmentally friendly benzylation of arenes with benzyl ethers as benzyl donors using BF3-Et2O to generate in situ the superacid BF3-H2O as an efficient promotor has been described. A wide variety of functional groups have been investigated and found to be compatible to give the desired diarylmethanes in yields of up to 99%. The crucial role of the moisture content in this transformation has been demonstrated by detailed investigations. This journal is the Partner Organisations 2014.