30567-87-4

Usage

Uses

Used in Organic Chemistry:
(2-Methoxyphenyl)-(4-methoxyphenyl)-methane is used as a starting material for the synthesis of other organic compounds and pharmaceuticals. Its unique structure allows for various chemical reactions and modifications, making it a versatile building block in organic chemistry.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2-Methoxyphenyl)-(4-methoxyphenyl)-methane serves as a precursor for the development of new pharmaceuticals. Its chemical properties and reactivity enable the creation of novel drug candidates with potential therapeutic applications.
Used in Fragrance Manufacturing:
(2-Methoxyphenyl)-(4-methoxyphenyl)-methane is used as a fragrance ingredient in perfumes and personal care products. Its aromatic properties contribute to the overall scent profile of these products, enhancing their appeal to consumers.
Used in Pharmaceutical Industry:
(2-Methoxyphenyl)-(4-methoxyphenyl)-methane is used as a starting material for the development of new pharmaceuticals in the pharmaceutical industry. Its unique structure and reactivity make it a valuable component in the synthesis of potential drug candidates.
Used in Perfume and Personal Care Products Industry:
In the perfume and personal care products industry, (2-Methoxyphenyl)-(4-methoxyphenyl)-methane is used as a fragrance ingredient. Its aromatic properties add depth and complexity to the scents of perfumes and personal care products, making them more attractive to consumers.

InChI:InChI=1/C15H16O2/c1-16-14-9-7-12(8-10-14)11-13-5-3-4-6-15(13)17-2/h3-10H,11H2,1-2H3

Upstream product

• 2467-03-0 2-[(4-hydroxyphenyl)methyl]phenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 30567-86-3 (2-methoxyphenyl)(4-methoxyphenyl)methanol 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 100-66-3 methoxybenzene 
• 824-94-2 p-methoxybenzyl chloride 
• 625-45-6 2-methoxyacetic acid 
• 7647-01-0 hydrogenchloride 
• 612-16-8 (2-methoxyphenyl)methanol 
• 766-51-8 2-Chloroanisole 
• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 50-00-0 formaldehyd 
• 58774-83-7 [(2-methoxyphenyl)methyl]dimethylamine 

Downstream Products

• 5449-69-4 2,4'-dimethoxybenzophenone 
• 100-09-4 4-methoxybenzoic acid 
• 105170-31-8 L-3,5-Diiodo-3'-(4-hydroxybenzyl)-thyronine 
• 105170-33-0 L-3,5-diiodo-3'-(4-methoxybenzyl)-O-methyl-N-trifluoroacetyl thyronine methyl ester 
• 105170-37-4 2,4'-dimethoxy-5-thiocyanodiphenylmethane 

Relevant academic research and scientific papers

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.

Preparation method of diarylmethane structure compound

The invention discloses a preparation method of a diarylmethane structure compound. The preparation method disclosed by the invention is as shown in a formula I, and a target compound is prepared through reaction of benzyl alcohol and an aryl electrophilic reagent by utilizing a cheap metal nickel catalyst, taking 1, 1 '-bis (diphenylphosphine) ferrocene and 1, 10-phenanthroline as ligands, takingdimethyl oxalate as an additive and taking manganese powder as a reducing agent. The method has the advantages of easily available raw materials, mild reaction conditions, wide reaction substrate, good compatibility of reaction functional groups, unique chemical selectivity and the like. The method not only can be used for preparing the simple diarylmethane compound, but also can be suitable formodifying bioactive molecules with similar structures of raw materials.

Sc(OTf)3-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source

Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)3 as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.

Palladium-Catalysed Cross-Coupling of Benzylammonium Salts with Boronic Acids under Mild Conditions

Herein, we give a full account of the development of the palladium-catalysed cross-coupling of benzylammonium salts with boronic acids. A range of benzylamine-derived quaternary ammonium salts can be coupled with boronic acids under relatively mild conditions. Our optimization has identified ligands that can be used to chemoselectively cross-couple at the ammonium in the presence of chlorides. We demonstrate that intramolecular palladium-catalysed C-H activation is also a viable pathway for the putative benzyl-Pd(II) intermediate obtained upon oxidative addition and have optimised this to obtain fluorene in good yield.

Biotransformation of isofraxetin-6-O-β-D-glucopyranoside by Angelica sinensis (Oliv.) Diels callus

Isofraxetin-6-O-β-D-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes. As a result, 15 products were yielded from the suspension cultures, including a new coumarin: 8′-dehydroxymethyl cleomiscosin A (1), together with 14 known compounds. Their structures were elucidated by extensive spectroscopic analysis. Furthermore, the biotransformed pathways were discussed. Among them, compound 13 was transformed from isofraxetin-6-O-β-D-glucopyranoside, while compounds 1–6, 10–12, 14–15 were derived from the culture medium stimulated by the substrate. The biotransformation processes include hydroxylation, oxidation and esterification. Furthermore, their inhibitory effects on lipopolysaccharide (LPS)-activated nitric oxide (NO) production were evaluated in BV2 microglial cells. It is worth noting that, 1, 1′-methanediylbis(4-methoxybenzene) (3), obtucarbamates A (5), 2-nonyl-4-hydroxyquinoline N-oxide (10) and 1H-indole-3-carbaldehyde (11) exhibited significant inhibitory effect against neuroinflammation with IC50values at 1.22, 10.57, 1.02 and 0.76?μM respectively, much stronger than that of the positive control minocycline (IC5035.82?μM).

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.

Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers

Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance.

Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: Stereospecific formation of diarylethanes via C-N bond activation

We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.

Tin exchanged heteropoly tungstate: An efficient catalyst for benzylation of arenes with benzyl alcohol

The partial exchange of tin with the protons of 12-tungstophosphoric acid (TPA) results in a highly active heterogeneous catalyst for benzylation of arenes with benzyl alcohol as benzylating agent. The catalysts were characterized by X-ray diffraction, Laser-Raman and FT-IR of pyridine adsorption. The catalytic activity depends significantly on the extent of tin exchanged with the protons of heteropoly tungstate. The characterization results suggest the presence of Lewis acidic sites by the exchange of tin. The catalyst with partial exchange of Sn showed high benzylation activity, which in turn related to variation in acidity of the catalysts. The catalyst is highly active for benzylation reaction irrespective of the nature of substituted arenes and benzyl alcohols. These catalysts are highly active compared to other acid catalysts used for benzylation of different arenes. The catalyst is easy to separate from reaction mixture and exhibit consistent activity upon reuse. The plausible reaction mechanism based on the role of both Lewis and Bronsted acid sites of the catalyst was discussed.

Dual-reagent catalysis within Ir-Sn domain: Highly selective alkylation of arenes and heteroarenes with aromatic aldehydes

(Chemical Equation Presented) Reactions of arenes and heteroarenes with aromatic aldehydes proceeded smoothly in the presence of a catalytic combination of [Ir(COD)Cl]2-SnCl4 to afford the corresponding triarylmethane derivatives (TRAMs) in high yields. This 100% TRAM selective transformation is clean and eliminates the use of acid systems.