31574-11-5

Usage

Chemical class

Chlorobenzenes and benzyl ethers

Physical state

Clear, colorless liquid

Molecular weight

232.68 g/mol

Applications

a. Organic synthesis
b. Building block for pharmaceutical compounds and agrochemicals
c. Production of 4,4'-dimethoxybenzophenone (used in optical brighteners and UV absorbers)
d. Synthesis of pharmaceuticals and fragrances
e. Intermediate in the synthesis of other important compounds

Hazardous material

Yes, can cause skin and eye irritation upon contact

Safety precautions

Handle with care and use appropriate protective equipment

Upstream product

• 106-39-8 bromochlorobenzene 
• 824-94-2 p-methoxybenzyl chloride 
• 500891-83-8 benzyl 4-chlorophenyl carbonate 
• 31558-46-0 4-methoxybenzyl phenyl carbonate 
• 106-48-9 4-chloro-phenol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 31558-47-1 p-Methoxybenzyl-p-chlorphenyl-carbonat 

Downstream Products

• 106-48-9 4-chloro-phenol 

Relevant academic research and scientific papers

A Unified and Practical Method for Carbon–Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis

While carbon–heteroatom cross-coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C?O, C?N and C?S cross-coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel(II) complex, is responsible for the key reductive elimination step that couples aryl bromides, iodides, and chlorides to 1° and 2° alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.

A practical method for p -methoxybenzylation of hydroxy groups using 2,4,6-tris(p -methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)

A new acid-catalyzed p-methoxybenzylating reagent, 2,4,6-tris(p- methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM), has been developed. The reaction of acid- and alkali-labile alcohols with TriBOT-PM in the presence of a catalytic amount of various acids (TfOH, BF3·OEt2, CSA, etc.) afforded the corresponding p-methoxybenzyl ethers in good yields. Since TriBOT-PM is an air-stable crystalline solid and can be prepared from inexpensive materials, i.e. cyanuric chloride and anisyl alcohol, this route is of practical use. Georg Thieme Verlag Stuttgart, New York.

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.

The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans

The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd2dba3 and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H2O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances, this protocol overcomes limitations in existing Pd-catalyzed coupling reactions of aliphatic alcohols with aryl halides. Finally, we demonstrate that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes. Copyright