13865-56-0

Basic information

• Product Name: 1-benzhydryl-4-methoxy-benzene
• Synonyms: 4-Benzhydrylanisole;4-Methoxytriphenylmethane;4-Methoxy-1-benzhydrylbenzene;1-Methoxy-4-benzhydrylbenzene;1-Benzhydryl-4-methoxybenzene;(4-Methoxyphenyl)diphenylmethane;Benzene, 1-(diphenylmethyl)-4-methoxy-
• CAS NO: 13865-56-0
• Molecular Formula: C₂₀H₁₈O
• Molecular Weight: 274.3563
• Mol File: 13865-56-0.mol
• Article Data: 47

Chemical Properties

• Melting Point: 66-67 °C
• Boiling Point: 393.6°C at 760 mmHg
• Flash Point: 158.9°C
• Appearance: /
• Density: 1.068g/cm³
• Vapor Pressure: 4.79E-06mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 1-benzhydryl-4-methoxy-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzhydryl-4-methoxy-benzene(13865-56-0)
• EPA Substance Registry System: 1-benzhydryl-4-methoxy-benzene(13865-56-0)

Safety Data

• Hazardous Substances Data: 13865-56-0(Hazardous Substances Data)

Usage

Description

1-Benzhydryl-4-methoxy-benzene, also known as 4-methoxytriphenylmethane, is an organic compound with a molecular structure that features a benzhydryl group attached to a methoxy-substituted benzene ring. It is characterized by its aromatic properties and potential applications in various industries due to its unique chemical structure.

Uses

Used in Liquid Crystal Display (LCD) Manufacturing:
1-Benzhydryl-4-methoxy-benzene is used as a key component in the manufacturing process of liquid crystal display devices. Its application is attributed to its ability to influence the alignment and orientation of liquid crystal molecules, which is crucial for the display's performance and image quality.
Used in Pharmaceutical Industry:
1-Benzhydryl-4-methoxy-benzene is used as a synthetic intermediate for preparing polynucleotide-poly(diol) conjugates, which have therapeutic applications. The compound's role in this process is to facilitate the formation of stable and biocompatible conjugates that can be used for targeted drug delivery and gene therapy.

InChI:InChI=1/C20H18O/c1-21-19-14-12-18(13-15-19)20(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-15,20H,1H3

Upstream product

• 64-18-6 formic acid 
• 847-83-6 p-methoxytrityl alcohol 
• 67-56-1 methanol 
• 37964-77-5 diphenyl(4-methoxyphenyl)acetonitrile 
• 596-43-0 bromo-triphenyl-methane 
• 124-41-4 sodium methylate 
• 14470-28-1 mono-4-methoxytrityl chloride 
• 64-19-7 acetic acid 
• 7601-90-3 perchloric acid 
• 574-42-5 benzhydryl ether 
• 100-66-3 methoxybenzene 
• 91-01-0 1,1-Diphenylmethanol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 791-92-4 4-benzhydrylphenol 

Downstream Products

• 611-94-9 4-Methoxybenzophenone 
• 119-61-9 benzophenone 
• 971-92-6 (3-bromo-4-methoxyphenyl)diphenylmethanol 
• 78239-14-2 ((3-bromo-4-methoxyphenyl)methylene)dibenzene 

Relevant articles and documents

Triggering the approach of an arene or heteroarene towards an aldehyde via Lewis acid-aldehyde communication

The present work reports a combined experimental/computational study of the Lewis acid promoted hydroxyalkylation reaction involving aldehyde and arene/heteroarene and reveals a mechanism in which the rate determining aldehyde to alcohol formation via a four-member cyclic transition state (TS) involves a transfer of hydrogen from arene/heteroarene C-H to aldehyde oxygen with the breaking of the C-H bond and formation of C-C and O-H bonds. The effect of different Sn(iv) derivatives on the hydroxyalkylation reaction from different in situ NMR and computational studies reveals that although the exergonic formation of the intermediate and its gained electrophilicity at the carbonyl carbon drive the reaction in SnCl4 compared to other Sn(iv) derivatives, the overall reaction is low yielding because of its stable intermediate. With respect to different aldehydes, LA promoted hydroxylation was found to be more feasible for an electron withdrawing aldehyde compared to electron rich aldehyde because of lower stability, enhanced electrophilicity gained at the aldehyde center, and a lower activation barrier between its intermediate and TS in the former as compared to the latter. The relative stability of the LA-aldehyde adduct decreases in the order SnCl4 > AlCl3 > InCl3 > BF3 > ZnCl2 > TiCl4 > SiCl4, while the activation barrier (ΔG#) between intermediate and transition states increases in the order AlCl3 4 3 3 4 2 4. On the other hand, the activation barriers in the case of different arenes/heteroarenes are in the order of indole 3, InCl3 and SnCl4 because they have negative free energy of formation (ΔG) for alcohol to the corresponding diaryl methyl carbocation.

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Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters

The synthesis of triarylmethanes via Pd-catalyzed Suzuki-Miyaura reactions between diarylmethyl 2,3,4,5,6-pentafluorobenzoates and aryl boronic acids is described. The system operates under mild conditions and has a broad substrate scope, including the coupling of diphenylmethanol derivatives that do not contain extended aromatic substituents. This is significant as these substrates, which result in the types of triarylmethane products that are prevalent in pharmaceuticals, have not previously been compatible with systems for diarylmethyl ester coupling. Furthermore, the reaction can be performed stereospecifically to generate stereoinverted products. On the basis of DFT calculations, it is proposed that the oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrate occurs via an SN2 pathway, which results in the inverted products. Mechanistic studies indicate that oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrates to (IPr)Pd(0) results in the selective cleavage of the O-C(benzyl) bond in part because of a stabilizing η3-interaction between the benzyl ligand and Pd. This is in contrast to previously described Pd-catalyzed Suzuki-Miyaura reactions involving phenyl esters, which involve selective cleavage of the C(acyl)-O bond, because there is no stabilizing η3-interaction. It is anticipated that this fundamental knowledge will aid the development of new catalytic systems, which use esters as electrophiles in cross-coupling reactions.

An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols

This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki Coupling of Trimethylammonium Salts and Arylboronic Acids

An efficient palladium-catalyzed Suzuki coupling of 1,1-diarylmethyl-trimethylammonium triflates with arylboronic acids is reported. This reaction offers a novel approach to triarylmethane derivatives in good to excellent yields with the palladium-catalyzed C-N bond cleavage as the key feature. Broad substrate scope regarding both reaction partners are observed. Moreover, reactive functional groups such as vinyl and formyl groups are conserved in this transformation.