793-23-7

Usage

Physical state

Colorless to pale yellow liquid

Odor

Faint

Solubility

Insoluble in water, soluble in organic solvents

Uses

a. Monomer in the production of polymers and resins
b. Manufacturing of specialty plastics, adhesives, and coatings
c. Chemical intermediate in the synthesis of various organic compounds

Toxicity

Low toxicity, generally regarded as safe for industrial and commercial applications

Safety precautions

Proper safety precautions should be taken when handling 1,4-dibenzylbenzene

InChI:InChI=1/C20H18/c1-3-7-17(8-4-1)15-19-11-13-20(14-12-19)16-18-9-5-2-6-10-18/h1-14H,15-16H2

Upstream product

• 101-81-5 Diphenylmethane 
• 38632-84-7 benzyl benzenesulfonate 
• 14297-39-3 4-benzylbenzyl chloride 
• 4301-15-9 ethynyldimagnesium dibromide 
• 100-39-0 benzyl bromide 
• 71-43-2 benzene 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 
• 538-86-3 benzyl methyl ether 
• 50-00-0 formaldehyd 
• 109-87-5 Dimethoxymethane 
• 4497-29-4 bis(bromomethyl) ether 
• 2467-18-7 boric acid tribenzyl ester 
• 539-30-0 1-(ethoxymethyl)benzene 

Downstream Products

• 3016-97-5 1,4-dibenzoylbenzene 
• 611-95-0 4-carboxybenzophenone 
• 52207-04-2 1,4-bis-(α-hydroxyimino-benzyl)-benzene 
• 66837-44-3 1,4-bis(α-bromobenzyl)benzene 
• 102007-33-0 1,4-bis-(4-nitro-benzyl)-benzene 
• 18908-95-7 C₄₀H₃₄O₆ 
• 82639-42-7 α,α'-diphenyl-α-bromo-p-xylene 
• 793-22-6 1,4-Bis-cyclohexylmethyl-cyclohexan 
• 896-11-7 1,4-Bis-cyclohexylmethyl-benzol 
• 31024-89-2 α,α'-diphenyl-1,4-benzenedimethanol 
• 95560-57-9 α,α'-diphenyl-1,4-benzenedimethanol diacetate 
• 15442-88-3 1,4-bis-(α,α-dichloro-benzyl)-benzene 
• 1308332-41-3 C₃₂H₃₆O₆ 
• 1308332-40-2 C₃₂H₃₆O₃ 

Relevant academic research and scientific papers

Convenient preparation of 1,4-dibenzylbenzene using zinc chloride in the presence of polar solvents

1,4-Dibenzylbenzene was successfully synthesized by the Friedel-Crafts benzylation of benzene with 1,4-bis(chloromethyl)benzene using zinc chloride in the presence of polar solvents. In particular, zinc chloride dissolved in primary alcohols or ketones with a molar ratio of 1 was a highly effective catalytic system in the reaction.

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions

Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.

Benzylation of benzene by benzyl chloride over silica-supported iron sulfate catalysts

The silica-supported Fe-containing catalysts prepared using FeSO 4 as a precursor exhibit high activity toward the reaction of benzene with benzyl chloride.

Synthesis of conjugated tri(hetero)aryl derivatives based on one-pot double Suzuki-miyaura couplings using bifunctional dipotassium phenylene-1,4- bis(trifluoroborate)

An efficient one-pot double Suzuki-Miyaura cross--coupling reaction between bifunctional phenylene-1,4-bis(potassium trifluoroborate) and aryl and heteroaryl bromides is described. The scope and limitations of this methodology that enables the synthesis o

Selective synthesis of 1,4-dialkylbenzenes from terephthalic acid

Terephthalic acid reacts with alkyl halides under Birch conditions to substituted 1,4-cyclohexadienes in high yields and good stereoselectivities. Electrophiles containing ester or nitrile groups undergo a surprising fragmentation under the reaction conditions. Subsequent treatment with chlorosulfonic acid proceeds by an interesting tandem decarbonylationldecarboxylation, affording 1,4-dialkylbenzenes in excellent regioselectivity. Thus our new method is superior to classical Friedel-Crafts alkylations.

Palladium-catalyzed synthesis of diarylmethanes: Exploitation of carbanionic leaving groups

A novel route to the synthesis of diarylmethanes via a Pd-catalyzed α-arylation of benzyl ketones is rseported. By harnessing the inherent reactivity of enolates, it is possible to circumvent the need for a transmetalating reagent such as boron for the co

New method for the reduction of benzophenones with Raney Ni-Al alloy in water

Raney Ni-Al alloy in a dilute alkaline aqueous solution has been shown to be a powerful reducing agent, which is highly effective in the reduction of benzophenones to the corresponding hydrocarbon derivatives, in the absence of any organic solvents. Copyright Taylor & Francis Group, LLC.

Friedel-crafts benzylation of arenes over mixed oxides

The replacement of liquid acid catalyst by solid acids for the Friedel-Crafts reaction of aromatic alkylation is a challenging task. Mixed oxide possessing spinel structures were found to catalyze the Friedel-Craft benzylation of arenes. It was found that the reaction was very fast at 80 °C, hence the reaction was studied with respect to more substrate. The significant point was even at this temperature monobenzylation, with the para isomer predominating, was achieved. Mixed oxides were prepared by co-precipitation method and were characterized by XRD technique.

Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions

A highly efficient Suzuki cross-coupling reaction between benzylic halides and aryl boronic acids using palladium chloride as catalyst in acetone:water (3:1) has been developed. High yields of products, mild reaction conditions and short reaction times in the absence of ligand are important features of this method. A highly efficient Suzuki cross-coupling reaction between benzylic halides and aryl boronic acids using palladium chloride as catalyst in acetone:water (3:1) as the solvent system has been developed. High yields of products, mild reaction conditions and short reaction times in the absence of ligand are important features of this method.

Suzuki cross-coupling reaction of benzylic halides with arylboronic acids in the presence of a tetraphosphine/palladium catalyst

The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane-[PdCl(C3H5)]2 system catalyses efficiently the Suzuki cross-coupling reaction of benzylic halides with arylboronic acids. A wide variety of benzylic bromides or chlorides and functionalised arylboronic acids lead selectively to the corresponding diarylmethane adducts in good yields. Furthermore, this catalyst can be used at low loading in many cases.