620-83-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 6121, 1988 DOI: 10.1016/S0040-4039(00)82282-0

InChI:InChI=1/C14H14/c1-12-7-9-14(10-8-12)11-13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 134-84-9 4-Methylbenzophenone 
• 131-58-8 2-Methylbenzophenone 
• 1517-63-1 4-methylphenyl(phenyl)methanol 
• 100-39-0 benzyl bromide 
• 108-88-3 toluene 
• 917-64-6 methyl magnesium iodide 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 694-53-1 phenylsilane 
• 42289-57-6 α-p-tolylbenzyl cation 
• 104-87-0 4-methyl-benzaldehyde 
• 71-43-2 benzene 
• 76312-48-6 2-phenyl-2-p-tolyl-[1,3]dithiolane 
• 100-52-7 benzaldehyde 

Downstream Products

• 1882-56-0 2-(4-methylphenyl)-2-phenylacetic acid 
• 134-84-9 4-Methylbenzophenone 
• 75790-82-8 (4-methyl-3-nitro-phenyl)-(4-nitro-phenyl)-methane 
• 106-42-3 para-xylene 
• 30203-93-1 4-[(4-methylphenyl)methyl]-1,1’-biphenyl 
• 113470-39-6 2-((4-methylphenyl)methyl)biphenyl 
• 84903-97-9 1-(tert-butyl)-4-(4-methylbenzyl) benzene 
• 115848-38-9 4-(3-tert-butylbenzyl)toluene 
• 125847-14-5 2-(4-fluorophenyl)-2-methyl-1-(4-methylphenyl)-1-phenylpropane 
• 86846-61-9 (4-Methyldiphenylmethyl)lithium 
• 16252-08-7 C₃₆H₃₄ 
• 611-95-0 4-carboxybenzophenone 
• 100224-75-7 4-methyl-2-nitro-benzophenone 
• 66826-95-7 1-(cyclohexylmethyl)-4-methylcyclohexane 

Relevant academic research and scientific papers

REACTIVE FORM OF 12-MOLYBDOSILICATE CATALYST ON FRIEDEL-CRAFTS-TYPE REACTION

Stepwise replacement of protons in H4 by tetrabutylammonium cation and catalysis by the replaced compounds for alkylation of toluene with benzyl chloride have been investigated.Only threeprotonated compound showed comparable activity with that of parent one.

Selective Friedel-Crafts Alkylation on a Vermiculite, a Highly Active Natural Clay Mineral with Lewis Acid Sites

Acid-catalyzed Friedel-Crafts alkylation reactions of p-methylbenzyl chloride with benzene were carried out on four unmodified natural clay minerals.Phenyl-p-tolylmethane was quickly and selectively formed in the presence of vermiculite.Although the speci

High alkylation activities of ball-milled synthesized low-load supported iron oxide nanoparticles on mesoporous aluminosilicates

Low-load iron oxide nanoparticles on Al-SBA-15 prepared using a novel dry milling approach exhibited excelling activities in the microwave-assisted akylation of toluene with benzyl chloride (Lewis acids promoted reaction) and benzyl alcohol (Br?nsted acids promoted reaction) as compared to the parent Al-SBA-15 and similar iron oxide nanoparticles supported on Al-MCM-41 materials. Materials prepared using the milling protocol possessed remarkably low iron loadings (0.1 wt%) but featured highly accessible sites and small nanoparticle sizes that seemed to be related to the observed differences in activities in the systems.

Sulfated and phosphated mesoporous Nb oxide in the benzylation of anisole and toluene by benzyl alcohol

Materials possessing the high acidities of sulfated zirconia and the diffusion properties of mesoporous oxides are predicted to have numerous applications in the petrochemical industry. Because of surface deactivation and loss of structure under highly acidic conditions, there are few examples of materials which meet these specifications. In this work, mesoporous Nb oxide was treated with 1 M sulfuric acid or phosphoric acid and evaluated for their catalytic activities in the benzylation of toluene or anisole with benzyl alcohol. Characterization by XRD, nitrogen adsorption/desorption, and TEM demonstrated that the mesostructure was surprisingly stable to acid treatment. Pyridine adsorption and infrared spectroscopy (IR) showed a mixture of Lewis and Bronsted sites before and after acid treatment. Titration with a series of indicators demonstrated that sulfated mesoporous Nb oxide possesses a pKa of -8.2 and 31.784 mmol/g acid sites, roughly 100 times stronger than either bulk phosphated or sulfated niobia, which both possess pKa values in the range of -3.0. The best catalytic results in this study were achieved when using mesoporous Nb oxide treated with sulfuric acid; the conversion of benzyl alcohol with anisole to the benzylation product was 100% in 30 min, which is 200 times faster than the bulk catalyst. The extremely high activity was rationalized by the high number of strong Bronsted sites on the surface coupled with the superior diffusion properties of the mesoporous system. Copyright

One-pot synthesis of phenylmethanes using Al3+ doped and natural clays

New simple alternatives to produce phenylmethanes using toluene and toluene derivatives are reported; such processes are catalyzed by a natural and a doped Al3+ Mexican bentonitic earth. The clays show a dual catalytic effect, as inductors of free radicals and as catalysts of electrophilic aromatic substitution. The catalytic effect as well as some physical and chemical properties of the clays are also reported.

Hydrothermal etching assisted crystallization: A facile route to functional yolk-shell titanate microspheres with ultrathin nanosheets-assembled double shells

We report a facile "hydrothermal etching assisted crystallization" route to synthesize Fe3O4@titanate yolk-shell microspheres with ultrathin nanosheets-assembled double-shell structure. The as-prepared microspheres possess a uniform size, tailored shell structure, good structural stability, versatile ion-exchange capability, high surface area, large magnetization, and exhibit a remarkable catalytic performance.

Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H3PO3/I2

For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel-Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.

Development of highly efficient Friedel-Crafts alkylations with alcohols using heterogeneous catalysts under continuous-flow conditions

The development of Friedel-Crafts alkylations with alcohols under continuous-flow conditions using heterogeneous catalysts is reported. The reactivities and durabilities of the examined catalysts were systematically investigated, which showed that montmorillonite clay is the best catalyst for these reactions. A high turnover frequency of 9.0 × 102h?1was recorded under continuous-flow conditions, and the continuous operation was successfully maintained over one week.

Multifunctional oxygen vacancies in WO3–x for catalytic alkylation of C–H by alcohols under red-light

Surface reaction kinetics and light absorption properties of a photocatalyst are essential demands for efficiently solar to chemical energy converting. In this study, plasmonic WO3–x was firstly applied to photocatalytic alkylation of arenes under red light irradiation. The oxygen vacancies, both on the surface and in the bulk of WO3–x, allow abundant free electrons to increase carrier densities and support its LSPR using low energy photons. The surface oxygen vacancies have more functions: they not only release surface tungsten sites which ensure the chemisorption of alcohols due to the coordianation ability but also promote the activation of alcohols via an efficient transport of the holes on the neighbouring O sites to chemisorption alcohol species. In brief, the bulk oxygen vacancies provide abundant charges and the surface vacancies promote the bond adsorption and activation abilities, which ensure the high efficiency of photocatalytic alkylation of C–H.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.