Methyl 2-(3-chlorophenoxy)acetate
[CAS# 74411-14-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 2-(3-chlorophenoxy)acetate
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.62
• CAS Registry Number: 74411-14-6
• SMILES: COC(=O)COC1=CC(=CC=C1)Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

Methyl 2-(3-chlorophenoxy)acetate is a valuable chemical compound widely used in organic synthesis and pharmaceutical applications. The discovery of this compound can be traced back to the increasing interest in phenoxyacetates, which are known for their diverse biological activities and their utility as intermediates in the synthesis of various organic molecules. The introduction of the chlorophenyl group enhances the compound's properties, making it a subject of interest in medicinal chemistry.

The synthesis of methyl 2-(3-chlorophenoxy)acetate generally involves the nucleophilic substitution of methyl acetate with 3-chlorophenol. This reaction is typically catalyzed by a base, facilitating the formation of the ester linkage while preserving the chlorophenyl group. The resulting product is characterized by its distinct structural features, including an ester functional group and a chlorinated aromatic ring, which confer unique chemical reactivity and enhance the compound's lipophilicity.

One of the primary applications of methyl 2-(3-chlorophenoxy)acetate lies in medicinal chemistry, where it serves as an important intermediate in the synthesis of biologically active compounds. The presence of the chlorophenyl group often contributes to enhanced pharmacological properties, making derivatives of this compound valuable in drug development. For instance, analogs of methyl 2-(3-chlorophenoxy)acetate have been explored for their potential anti-inflammatory and anticancer activities, showcasing the compound's relevance in therapeutic applications.

Moreover, this compound is utilized in the agrochemical industry, where it acts as a precursor for the development of herbicides and pesticides. The introduction of halogenated aromatic groups in agrochemicals can improve the efficacy and selectivity of the active ingredients, leading to more effective crop protection solutions.

In addition to its applications in pharmaceuticals and agrochemicals, methyl 2-(3-chlorophenoxy)acetate is also employed in the synthesis of specialty chemicals and materials. Its unique chemical properties enable the design of novel compounds with tailored functionalities for specific applications in various industrial sectors.

In summary, methyl 2-(3-chlorophenoxy)acetate is a significant compound in organic chemistry, with its discovery and diverse applications highlighting the importance of chlorinated phenoxy derivatives in medicinal and agricultural chemistry. Ongoing research into its synthesis and application continues to reveal new opportunities for this versatile compound.