7249-83-4

Usage

Appearance

White to off-white crystalline solid

Odor

Faint, aromatic

Usage

Intermediate in production of fragrances, aromatic compounds, and pharmaceuticals

Applications

Automotive, electronics, cosmetics industries

Role in synthesis

Key component in synthesis of complex molecules with multiple aromatic rings

Additional uses

Stabilizer in polymers, additive in lubricants and oils

Upstream product

• 91-01-0 1,1-Diphenylmethanol 
• 106-42-3 para-xylene 
• 855869-12-4 (2,5-Dimethyl-phenyl)-diphenyl-methanol 
• 4044-60-4 2,5-dimethylbenzophenone 
• 776-74-9 Bromodiphenylmethane 
• 42100-74-3 ((octyloxy)methylene)dibenzene 
• 19672-37-8 3-benzhydryl-pentane-2,4-dione 
• 574-42-5 benzhydryl ether 
• 90-99-3 diphenylchloromethane 

Downstream Products

• 500698-13-5 5-methyl-3,3-diphenyl-phthalide 

Relevant academic research and scientific papers

Two-component boronic acid catalysis for increased reactivity in challenging Friedel-Crafts alkylations with deactivated benzylic alcohols

A general and efficient boronic acid catalyzed Friedel-Crafts alkylation of arenes with benzylic alcohols was previously developed for the construction of unsymmetrical diarylmethane products (X. Mo, J. Yakiwchuk, J. Dansereau, J. A. McCubbin and D. G. Hall, J. Am. Chem. Soc., 2015, 137, 9694). Highly electron-deficient benzylic alcohols, however, were ineffective coupling partners due to the increased difficulty of C-O bond ionization. Herein, we report the use of perfluoropinacol as an effective co-catalyst to improve the reactivity of a boronic acid catalyst in the Friedel-Crafts benzylations of electronically deactivated primary and secondary benzylic alcohols. According to spectroscopic studies, it is believed that perfluoropinacol condenses with the arylboronic acid catalyst to form a highly electrophilic and Lewis acidic boronic ester. This in situ formed species enables a more facile ionization of the benzylic alcohols likely through a mode of activation promoted by a Lewis acid assisted hydronium Br?nsted acid generated from the interactions of the transient boronic ester with hexafluoroisopropanol solvent and water.

Unmodified Fe3O4 nanostructure promoted with external magnetic field: safe, magnetically recoverable, and efficient nanocatalyst for N- and C-alkylation reactions in green conditions

Transition metal compounds have emerged as suitable catalysts for organic reactions. Magnetic compounds as soft Lewis acids can be used as catalysts for organic reactions. In this report, the Fe3O4 nanostructures were obtained from Fe2+ and Fe3+-salts, under an external magnetic field (EMF) without any protective agent. The X-ray photoelectron spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectroscopy tools were used to characterize these magnetic compounds. The two-dimensional (2-D, it showed nanometric size in the two dimensions, nanorod structure) Fe3O4 compound showed high catalytic activity and stability in N- and C-alkylation reactions. A diverse range of N- and C-alkylation products were obtained in moderate to high yield under green and mild conditions in air. Also the N- and C-alkylation products can be obtained with different selectivity and yield by exposure reactions with EMF. Results of alkylation reactions showed that the presence of Fe(II) and Fe(III) species on the surface of magnetic catalysts (phase structure of magnetic compounds) are essential as very cheap active sites. Also, morphology of magnetic catalysts had influence on their catalytic performances. After the reaction, the catalyst/product(s) separation could be easily achieved with an external magnet and more than 95% of catalyst could be recovered. The catalyst was reused at least four times without any loss of its high catalytic activity for N- and C-alkylation reactions.

SO3H-functionalized organic-inorganic ionic liquids based on polyoxometalates characterization and their application in C-C coupling reaction

Different ionic liquids (ILs) with SO3H as functional group were achieved by combining SO3H-functionalized organic cations and polyoxometalates (POM). The obtained salts were characterized and their catalytic activities investigated

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.

Simple Method for sp2-sp3 and sp3-sp3 Carbon-Carbon Bond Activation in 2-Substituted 1,3-Diketones

Simple and efficient methods were developed for sp2-sp3 and sp3-sp3 C-C bond-activation reactions of 2-substituted 1,3-diketones. 3-Substituted 3-bromopentane-2,4-diones were deacylated in the presence of an aromatic compound and a silica gel supported Bronsted acid containing sulfonic groups. The carbocation formed by cleavage of the sp3-sp3 C-C bond of the dione alkylated the aromatic compound.

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.

An improved method for the synthesis of triarylmethanes using heterogenized 12-tungestocobaltic acid

Two heterogeneous catalysts based on 12-tungestocobaltic acid, including K5CoW12O40 and H5CoW 12O40 supported on rice husk ash extracted nano silica (CoW/NSiO2), were used in sel

Superacid BF3-H2O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water

A convenient procedure employing simple starting materials benzyl alcohols and acetates as the benzyl donors to assemble a series of diarylalkanes through benzylation of arenes using in situ prepared superacid BF3-H 2O as an efficient promoter has been developed. The beneficial role of water in the reaction has been clarified with combination of control experiments and 11B NMR analysis. This reaction is a self-promoted model, which is triggered by the trace of water and continuously promoted by self released by-product water (or carboxylic acid). A wide range of substrates are investigated and the moderate to excellent yields and the good regioselectivities for secondary benzyl alcohols as well as arenes bearing electron-withdrawing groups have been achieved. As a result, moisture in the reaction system has been utilized as an efficient initiator in all benzylation cases.

Direct alkylation of aromatics using alcohols in the presence of NaHSO 4/SiO2

Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could be recycled eight times without activity loss.

Iron oxide nanoparticles grown on carboxy-functionalized graphite: An efficient reusable catalyst for alkylation of arenes

Here we report a simple procedure for the synthesis of a novel hybrid catalyst by growing iron oxide nanoparticles on carboxy-functionalized graphite. This hybrid catalyst demonstrated superior catalytic activity towards the alkylation of arenes with alkyl halides in contrast to commercial graphite or unsupported iron oxide nanoparticles in terms of yields and general applicability. The catalyst can be reused up to five times with a minimal loss of catalytic activity. Georg Thieme Verlag Stuttgart.