19962-25-5

Usage

Type of compound

Benzene derivative

Attached groups

Chlorine atom and phenoxy group

Common uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Additional uses

Precursor in the production of dyes, polymers, and other industrial chemicals

Physical state

Colorless liquid

Odor

Slightly aromatic

Toxicity

Moderately toxic

Safety precautions

Handle with care, store in a cool, well-ventilated area away from heat sources and incompatible materials

Upstream product

• 352-12-5 4-chlorobenzyl fluoride 
• 139-02-6 sodium phenoxide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 104-88-1 4-chlorobenzaldehyde 
• 108-95-2 phenol 
• 108-88-3 toluene 
• 622-95-7 4-chlorobenzyl bromide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 873-76-7 para-Chlorobenzyl alcohol 
• 591-50-4 iodobenzene 
• 108-90-7 chlorobenzene 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 

Downstream Products

• 104-88-1 4-chlorobenzaldehyde 
• 108-95-2 phenol 
• 55631-11-3 1-chloro-4-(1-phenoxypropyl)benzene 
• 872415-75-3 (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(benzyl)iridium(III) 
• 1326725-12-5 (p-chlorobenzyl)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III) 
• 884188-41-4 1-chloro-4-[(4-iodophenoxy)methyl]benzene 

Relevant academic research and scientific papers

Developing benign syntheses using ion pairsviasolvent-free mechanochemistry

Solvent-free mechanochemical conditions have been developed to investigate the significance of ion pairing and the use of weak bases for driving forward nucleophilic substitution reactions. This approach takes advantage of the lack of solvent shells to in

CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions

Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].

Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates

A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.

Palladium nanoparticles supported on cysteine-functionalized MNPs as robust recyclable catalysts for fast O- and N-arylation reactions in green media

A magnetically robust recyclable nanocatalyst was fabricated by immobilizing of Pd onto the surface of cysteine-functionalized magnetic nanoparticles (MNPs?Cys-Pd). This nanocatalyst was characterized using various techniques such as FT-IR, XRD, TEM, SEM, EDX, VSM, and ICP. The application of catalyst (MNPs?Cys-Pd) was investigated for O-arylation and N-arylation reactions. This phosphine-free complex was found as highly efficient heterogeneous catalyst in green media and mild reaction conditions. In addition, it gave excellent recyclability without significant deactivation after ten cycles.

From insertion to multicomponent coupling: Temperature dependent reactions of arynes with aliphatic alcohols

The temperature dependent selectivity switch in the reaction of arynes with aliphatic alcohols in THF has been reported. At -20°C, arynes smoothly insert into the O-H bond of alcohols to form alkyl aryl ethers. Interestingly, at 60°C, a highly selective multicomponent coupling occurs with the solvent THF acting as the nucleophilic trigger affording (4-(alkoxy)butoxy)arenes.

α-Lithiated Aryl Benzyl Ethers: Inhibition of [1,2]-Wittig Rearrangement and Application to the Synthesis of Benzo[b]furan Derivatives

The use of t-BuLi at low temperature selectively leads to α-lithiation of benzyl phenyl ether generating a stable organolithium, which can be efficiently trapped with a variety of selected electrophiles prior to suffering the expected [1,2]-Wittig rearrangement. In the case of (o-alkynyl)phenyl benzyl ethers, the intermediate α-aryloxyorganolithium undergoes an unexpected anti intramolecular carbolithiation reaction leading to functionalized benzo[b]furan derivatives.

Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols

Deep eutectic solvents (such as the combination of urea and choline chloride) are found to be promising solvent and phase-transfer-media for benzylation of phenol. These methods avoided the complexity of multiple alkylations giving selectively O-alkylated aromatic products. Good to excellent yields of the corresponding benzyl phenyl ether were obtained. The non-toxic, biodegradable, inexpensive, and recyclable nature of DES make this protocol green and cost-effective.

Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition

Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.

Benzyl protection of phenols under neutral conditions: Palladium-catalyzed benzylations of phenols

Benzyl protection of phenols under neutral conditions was achieved by using a Pd(n3-C3H5)Cp-DPEphos catalyst. The palladium catalyst efficiently converted aryl benzyl carbonates into benzyl-protected phenols through the decarboxylative etherification. Alternatively, the nucleophilic substitution of benzyl methyl carbonates with phenols proceeded In the presence of the catalyst, yielding aryl benzyl ethers.

Ionic liquids as reagent and reaction medium: Preparation of alkyl aryl ethers

Room temperature ionic liquid, [bmIm]OH, is used as a green recyclable reaction medium and reagent for the alkylation of phenols in excellent yields. The recovered ionic liquid was reused five to six times with consistent activity.