14804-26-3

Usage

Molecular weight

184.67 g/mol

Aromatic compound

Consists of a benzene ring with a chlorine atom at one position, a methoxy group at another, and two methyl groups at the remaining positions.

Usage

Commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other fine chemicals. Also used in the production of fragrances and flavoring agents.

Reactivity

Versatile reactivity makes it an important intermediate in organic synthesis and of interest to researchers and industry alike.

Upstream product

• 2944-49-2 2,3-dimethylanisole 
• 1570-76-9 2,3-dimethyl-4-chlorophenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1022958-60-6 CEP-28122 
• 1354545-55-3 4-chloro-2,3-di(bromomethyl)anisole 
• 52855-18-2 2-(aminomethyl)-3,4-dichloro-5,6-dimethylphenol hydrobromide 
• 52780-52-6 2-chloro-N-<(5,6-dichloro-2-methoxy-3,4-dimethylphenyl)methyl>acetamide 

Relevant academic research and scientific papers

Selective aromatic chlorination of activated arenes with sodium chlorite, (salen)manganese(III) complex, and alumina in dichloromethane

The reaction of alkyl phenyl ethers with sodium chlorite in dichloromethane in the presence of a (salen)manganese(III) complex and alumina preloaded with a small amount of water afforded monochlorination products with unusually high para selectivities under mild conditions. The NaClO2-based biphasic system can also be successfully used for the regioselective monochlorination of substituted anisoles and polymethoxybenzenes.

Development and scale-up of an optimized route to the ALK inhibitor CEP-28122

Evolution of the process strategies to prepare CEP-28122, an anaplastic lymphoma kinase (ALK) inhibitor, is presented. The initial medicinal chemistry route, used for the preparation of key supplies for biological screening, is reviewed. In addition, the

Biphasic Electrophilic Halogenation of Activated Aromatics and Heteroaromatics with N-Halosuccinimides Catalyzed by Perchloric Acid

Catalytic amounts of 70percent perchloric acid (0.1 - 10, mostly 0.1 - 1, mol percent, based on substrate) initiate the regioselective halogenation of activated aromatics and heteroaromatics with N-halosuccinimide (NXS, X = Cl or Br) in two-phase solid-liquid systems (NXS/hexane or NXS/CCl4) at room temperature to give ring-halogenated products in high yields.For example, thiophene is transformed to 2-halo or 2,5-dihalo derivatives (yield 82-98percent) using 1 or 2 equiv of NXS, respectively.Unsymmetrical 2,5-dihalothiophenes are obtained in 70-82percent yield by reacting 2-halothiophenes with an appropriate NXS.The reaction of 3-bromothiophene with NBS affords 2,3-dibromothiophene in 93-99percent yield. 1,3-Dimethoxybenzene and 2,3-dimethylanisole are halogenated regiospecifically at the 4-position to give the corresponding products in 81-94percent yield.