831-81-2

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORODIPHENYLMETHANE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to be easily modified and incorporated into complex molecular structures.
Used in Organic Synthesis:
4-CHLORODIPHENYLMETHANE is used as a starting material in organic synthesis for the preparation of a wide range of chemical products, including agrochemicals, dyes, and other specialty chemicals.
Used in Zinc-Catalyzed Benzylic C-H Bond Oxidation:
4-CHLORODIPHENYLMETHANE is used as a substrate in zinc-catalyzed benzylic C-H bond oxidation reactions to produce carbonyl-containing compounds with good yields, which are valuable in the synthesis of various target molecules.

Preparation

4-Chlorodiphenylmethane is produced by reacting p-chlorobenzyl chloride with benzene in the presence of zinc chloride as raw material.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4817, 1961 DOI: 10.1021/jo01070a010

InChI:InChI=1/C13H11Cl/c14-13-8-6-12(7-9-13)10-11-4-2-1-3-5-11/h1-9H,10H2

Upstream product

• 112-34-5 Diethylene glycol monobutyl ether 
• 55816-27-8 4-chlorobenzophenone hydrazone 
• 38321-18-5 Natrium-[2-(2-butoxy-aethoxy)-aethylat] 
• 101-81-5 Diphenylmethane 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 71-43-2 benzene 
• 134-85-0 4-chlorobenzophenone 
• 352-12-5 4-chlorobenzyl fluoride 
• 2484-99-3 4-chloro-thiobenzophenone 
• 6008-75-9 2-(4-chlorophenyl)-2-phenyl-1,3-dithiolane 
• 100-39-0 benzyl bromide 
• 108-90-7 chlorobenzene 
• 62673-31-8 benzyl(bromo)zinc 
• 112529-05-2 1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-ethoxy)-ethanesulfonic acid 4-chloro-phenyl ester 

Downstream Products

• 17964-29-3 4-(trimethylsilyl)diphenylmethane 
• 115848-35-6 1-(tert-butyl)-4-(4-chlorobenzyl)benzene 
• 115848-37-8 C₁₇H₁₉Cl 
• 1026082-44-9 1-[4-(4-chlorobenzyl)phenyl]ethan-1-one 
• 30203-95-3 3,4'-Dinitro-4-chlor-diphenylmethan 
• 1326231-74-6 1-((4-chlorophenyl)(phenyl)methyl)-1H-benzo[d]imidazole 
• 1425513-33-2 1-(4-chlorophenyl)-6-((4-chlorophenyl)(phenyl)methyl)-2,3-diphenyl-1H-indene 
• 1425513-35-4 1,2,3-tris(4-chlorophenyl)-6-((4-chlorophenyl)(phenyl)methyl)-1H-indene 
• 694457-23-3 1-chloro-4-(1-phenylbut-3-en-1-yl)benzene 
• 258277-20-2 N-tosyl-[(4-chlorophenyl)(phenyl)methyl]amine 
• 5267-40-3 N-[(4-chlorophenyl)(phenyl)methyl]acetamide 
• 23450-31-9 4-benzylbenzonitrile 

Relevant academic research and scientific papers

Method for reducing carbonyl reduction to methylene under illumination

The invention belongs to the technical field of organic chemical synthesis. The method comprises the following steps: (1) mixing the carbonyl compound and the amine compound in a solvent, reacting 3 - 6 under the illumination of 380 - 456 nm, the reaction system is low in toxicity, high in atom utilization rate 12 - 24h. and production efficiency, safe and controllable in reaction process and capable of simplifying the operation in the preparation and production process. At the same time, the residue toxicity of the reaction is minimized, the pollution caused by the production process to the environment is reduced, and the steps and operations of removing residues after the reaction are simplified. In addition, the reactant feedstock is readily available. The reactant does not need additional modification before the reaction, can be directly used for preparing production, simplifies the operation steps, and shortens the reaction route. The production cost is obviously reduced.

Mixed Alkyl/Aryl Diphos Ligands for Iron-Catalyzed Negishi and Kumada Cross Coupling Towards the Synthesis of Diarylmethane

Mixed alkyl/aryl diphos ligands have been prepared and their application in iron-catalyzed cross coupling of benzylic chlorides with diaryl zinc (Negishi) or aryl Grignard reagents (Kumada) towards the synthesis of diarylmethane has been evaluated. The iron?diphos catalytic system exhibited the enhanced activity and selectivity in the two coupling reactions. The electron-rich mixed PPh2/PCy2 ligands outperformed their symmetrical PPh2 congeners, and led to decreased homocoupling byproduct formation. It indicates that the electronic effect of the ligands plays an important role in the catalytic performance. The Fe catalyst supported by L8 bearing an electron-rich PCy2 substituent and a sterically demanding tert-butyl on ethene backbone exhibited the best catalytic performance and good functional group tolerance in the two cross coupling reactions.

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.

Borane-catalyzed C(sp3)-F bond arylation and esterification enabled by transborylation

The activation and functionalization of carbon- fluorine bonds represent a significant synthetic challenge, given the high thermodynamic barrier to C-F bond cleavage. Stoichiometric hydridoborane-mediated C-F functionalization has recently emerged, but is yet to be rendered catalytic. Herein, the borane-catalyzed coupling of alkyl fluorides with arenes (carbon-carbon bond formation) and carboxylic acids (carbon-oxygen bond formation) has been developed using transborylation reactions to achieve catalytic turnover. Successful C-C and C-O coupling across a variety of structurally and electronically differentiated arenes and carboxylic acids was achieved using 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) as the catalyst and pinacolborane (HBpin), with broad functional group tolerance. Experimental and computational studies suggest a mechanistic dichotomy for the carbon-carbon and carbon-oxygen coupling reactions. B-F transborylation (B-F/B-H metathesis) between F-B-9-BBN and HBpin enabled catalytic turnover for carbon-carbon bond formation, whereas direct exchange between the alkyl fluoride and acyloxyboronic ester (C-F/B-O metathesis) was proposed for carbon-oxygen coupling, where H-B-9-BBN catalyzed the dehydrocoupling of the carboxylic acid with HBpin.

Nitrenium Salts in Lewis Acid Catalysis

Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry. By contrast, electrophilic nitrogen-containing compounds are much rarer. Nitrenium cations are a new family of nitrogen-based Lewis acids, the reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations. These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover, these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture, allowing for benchtop transformations without the need to pretreat solvents.

Reductive Deamination with Hydrosilanes Catalyzed by B(C6F5)3

The strong boron Lewis acid tris(pentafluorophenyl)borane B(C6F5)3 is known to catalyze the dehydrogenative coupling of certain amines and hydrosilanes at elevated temperatures. At higher temperature, the dehydrogenation pathway competes with cleavage of the C?N bond and defunctionalization is obtained. This can be turned into a useful methodology for the transition-metal-free reductive deamination of a broad range of amines as well as heterocumulenes such as an isocyanate and an isothiocyanate.

Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes

AlSBA-15 catalysts possessing Br?nsted acid and Lewis acid-base bifunctionalities catalyze the direct arylation of benzyl alcohols to diarylmethanes with an 85% product yield through C-O bond activation. 2 and 4wt%AlSBA-15 catalysts have been synthesised by adopting a simple and efficient post-synthetic metal implantation route. The synthesised catalysts were characterized using XRD, N2 adsorption and desorption, 27Al MAS NMR, XPS, HR-TEM, NH3 and CO2-temperature-programmed desorption (TPD) and pyridine-transmission-FTIR spectroscopy techniques to confirm the existence of Br?nsted acid and Lewis acid-base bifunctionalities. Through various control experiments, it is verified that Br?nsted acid sites activate the benzyl alcohol and Lewis base sites interact with phenylboronic acid concurrently to accomplish the coupling reaction. In the recyclability study, 4wt%AlSBA-15 preserves its activity and stability up to 5 cycles. The 4wt%AlSBA-15 catalyst unlike homogeneous catalysts does not require additives, long reaction time and expensive metals.

Phosphonic acid mediated practical dehalogenation and benzylation with benzyl halides

For the first time, by using H3PO3/I2 system, various benzyl chlorides, bromides and iodides were dehalogenated successfully. In the presence of H3PO3, benzyl halides underwent electrophilic substitution reactions with electron-rich arenes, leading to a broad range of diarylmethanes in good yields. These transformations feature green, cheap reducing reagents and metal-free conditions. A possible mechanism was proposed.

Scalable Wolff-Kishner Reductions in Extreme Process Windows Using a Silicon Carbide Flow Reactor

A safe and scalable continuous flow strategy for Wolff-Kishner reductions that employs methanol as the solvent has been developed. The use of low-cost hydrazine as the reducing agent in combination with a caustic base provides an atom-efficient, environmentally friendly method for the deoxygenation of aldehydes and ketones to alkanes. Because of the required harsh and corrosive reaction conditions (200 °C, 50 bar), reactor materials such as stainless steel, glass, or any type of polymer have compatibility problems, rendering this process problematic on a production scale. The use of corrosion-resistant silicon carbide (SiC) as the reactor material opens up the possibility of performing Wolff-Kishner reductions on scale with a considerably improved safety profile. Methanol as the solvent significantly simplifies the workup procedure compared with the generally employed high-boiling solvents such as diethylene glycol. The continuous flow protocol was applied to a number of substrates and provided the desired products in good to high yields with space-time yields of up to 152 g L-1 h-1. In addition, a pharmaceutically valuable active pharmaceutical ingredient precursor was synthesized by employing this higherature/pressure Wolff-Kishner protocol.

Super electron donor-mediated reductive desulfurization reactions

The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.