39768-70-2

Usage

Uses

Used in Pharmaceutical Industry:
Benzene, 1-fluoro-4-[(4-methylphenyl)methyl]is used as a key building block for the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Benzene, 1-fluoro-4-[(4-methylphenyl)methyl]also serves as an important intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Safety Precautions:
Due to its toxic nature and potential carcinogenic properties, Benzene, 1-fluoro-4-[(4-methylphenyl)methyl]should be handled with caution. Exposure to large amounts can be harmful to human health, necessitating proper safety measures during its use and manipulation in both research and industrial settings.

Upstream product

• 617-86-7 triethylsilane 
• 459-57-4 4-fluorobenzaldehyde 
• 108-88-3 toluene 
• 104-81-4 4-Methylbenzyl bromide 
• 352-13-6 4-flourophenylmagnesium bromide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 104-82-5 4-Methylbenzyl chloride 
• 1575785-15-7 C₁₅H₂₃FO 
• 459-46-1 4-Fluorobenzyl bromide 
• 5720-05-8 4-methylphenylboronic acid 
• 84640-22-2 4-fluorobenzyl N,N-dimethylcarbamate 
• 352-33-0 1-Chloro-4-fluorobenzene 

Downstream Products

• 530-46-1 4-fluoro-4'-methylbenzophenone 

Relevant academic research and scientific papers

Heteroleptic Ni(II) Complexes Bearing a Bulky Yet Flexible IBiox-6 Ligand: Improved Selectivity in Cross-Electrophile Coupling of Benzyl Chlorides with Aryl Chlorides/Fluorides

A bisoxazoline-derived NHC known as IBiox-6 reacted smoothly with Ni[P(OEt)3]2Br2 and Ni(PPh3)2Br2 to give the respective heteroleptic Ni(II) complexes Ni(IBiox-6)[P(OEt)3]Br2 (1) and Ni(IBiox-6)(PPh3)Br2 (2) in yields of 60% and 71%. Their crystal structures were characterized to reveal a rare cis disposition of the IBiox-6 ligand to the phosphite ligand in 1, while 2 possessed the more common trans configuration. Both complexes catalyzed the cross-electrophile coupling of benzyl chlorides with aryl chlorides and fluorides in the presence of Mg turnings at 50 °C via a "real one-pot"procedure, featuring no requirement for temperature variation or portionwise addition of any coupling partner. In particular, complex 1 showed a better balance between the catalytic activity and selectivity. The scope of the procedure catalyzed by 1 and Mg turnings was investigated, providing a highly selective, simple, and practical approach to the synthesis of diarylmethanes with high steric hindrance and various functional groups, including oligo-diarylmethane with asymmetric structures.

Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones

An original metal-free procedure for the synthesis of biarylmethanes is disclosed herein. The reactions occur with high selectivity starting from aryl iodides and benzylic ketones in the presence of superbasic media (CsOH/DMSO). This procedure allows a straightforward access to a wide range of biarylmethane derivatives substituted with electron-withdrawing and -donating substituents.

A Zinc Catalyzed C(sp3)?C(sp2) Suzuki–Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates

The Suzuki–Miyaura (SM) reaction is one of the most important methods for C?C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr2, in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.

Benzylation of arenes with benzyl halides synergistically promoted by in situ generated superacid boron trifluoride monohydrate and tetrahaloboric acid

To examine the assembly methodology of diarylmethanes, a benzylation of (hetero)arenes with benzyl halides has been developed and various diarylmethanes were furnished with yields of up to 98% and regioselectivities of up to >99%. The complexation of the by-product halogen hydride with BF3·OEt2 generated the Bronsted acid BF3·HX (HBF3X, X=Cl or Br) in situ to synergistically promote the benzylation.

N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids

The Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids was achieved in an environmentally benign medium. Using water as the sole solvent, such transformation took place very well to give the desired diarylmethane derivatives in good to almost quantitative yields in the presence of a well-defined NHC-Pd(ii)-Im complex under mild conditions. It is worth noting here that this is the first example of benzyl carbamates used in coupling reaction, thus affording a new method for the formation of diarylmethanes by palladium-catalyzed C-O bond activation.

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.

Palladium-catalyzed desulfitative cross-coupling reaction of sodium sulfinates with benzyl chlorides

A palladium-catalyzed approach for the synthesis of diarylmethanes from sodium sulfinates and benzyl chlorides is described. Various aromatic sodium sulfinates were used as aryl sources via extrusion of SO2 and gave the diarylmethanes in moderate to good yields.

IRON BISPHENOLATE COMPLEXES AND METHODS OF USE AND SYNTHESIS THEREOF

The present application, relates to iron bisphenolate complexes and methods of use and synthesis thereof. The iron complexes are prepared from tridentate or tetradentate ligands of Formula I: wherein R1 and R2 are as defined herein. Also provided are methods and processes of using the iron bisphenolate complexes as catalysts in cross-coupling reactions and in controlled radical polymerizations.

Coupling of benzyl halides with aryl Grignard reagents catalyzed by iron(III) amine-bis(phenolate) complexes

Reaction of benzylamino-N,N-bis(2-methylene-4,6-di-tert-amylphenol), H 2L1, with anhydrous ferric chloride in the presence of a base yields FeCl(THF)L1 (1). In the solid state, complex 1 exists as a monomeric iron(III) species with a distorted trigonal bipyramidal geometry. Complex 1 is an air-stable, non-hygroscopic, single-component catalyst for C-C cross-coupling of aryl Grignard reagents with benzyl halides, including chlorides. Moderate to good yields of cross-coupled products can be obtained in diethyl ether at room temperature. Preliminary investigations include the screening of electron-donating and electron-withdrawing groups on both the benzylic substrate and the aryl Grignard reagent.

Exploiting boron-zinc transmetallation for the arylation of benzyl halides: What are the reactive species?

One step Beyond: The transmetallation reactions of ArB(OH)2 and Ar3B3O3 with Et2Zn are far more complicated than previously supposed, with solvent-dependent equilibria between ArB(OY)2 at one side and [RZn(solv)3][BR4] at the other (see picture). While the role of the highly reactive organozinc cation has not been implicated before, its importance for the activation of an otherwise sluggish class of electrophiles is shown. Copyright