2-Chloro-4-methylsulphonylbenzoic acid
[CAS# 53250-83-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 2-Chloro-4-methylsulphonylbenzoic acid
• Synonyms: 2-Chloro-4-(methylsulfonyl)benzoic acid
• Molecular Formula: C₈H₇ClO₄S
• Molecular Weight: 234.65
• CAS Registry Number: 53250-83-2
• EC Number: 406-520-8
• SMILES: CS(=O)(=O)C1=CC(=C(C=C1)C(=O)O)Cl

Properties

• Melting point: 191-196 °C

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H318
• Safety Statements: P264+P265-P280-P305+P354+P338-aP317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

2-Chloro-4-methylsulphonylbenzoic acid is an organic compound that has gained attention due to its role in various chemical and industrial applications. This compound, characterized by the presence of a chloro group, a methylsulfonyl group, and a carboxylic acid group attached to a benzene ring, offers unique chemical properties that make it useful in the synthesis of more complex molecules and in the development of specialized materials.

The discovery of 2-Chloro-4-methylsulphonylbenzoic acid can be traced back to the systematic study of benzoic acid derivatives, which has been an area of significant interest in organic chemistry. Benzoic acid, a simple aromatic carboxylic acid, has long been a building block for the synthesis of a wide range of compounds. By introducing various functional groups, such as chloro and methylsulfonyl groups, chemists have been able to tailor the reactivity and properties of these derivatives for specific applications.

One of the primary applications of 2-Chloro-4-methylsulphonylbenzoic acid is in organic synthesis. The compound's structure makes it a versatile intermediate in the synthesis of agrochemicals, pharmaceuticals, and specialty chemicals. The presence of the chloro group allows for nucleophilic substitution reactions, where the chlorine atom can be replaced by other functional groups, leading to the creation of more complex molecules. The methylsulfonyl group, known for its electron-withdrawing properties, enhances the reactivity of the benzene ring, making it more susceptible to various chemical transformations. This makes 2-Chloro-4-methylsulphonylbenzoic acid a valuable starting material in synthetic organic chemistry.

In the agrochemical industry, derivatives of 2-Chloro-4-methylsulphonylbenzoic acid are used in the development of herbicides and pesticides. The compound's ability to be modified through substitution reactions allows for the creation of molecules that can selectively target specific biological pathways in plants or pests, leading to effective control of weeds or insect populations. These derivatives often work by inhibiting key enzymes or disrupting critical metabolic processes, making them powerful tools in modern agriculture.

In the pharmaceutical industry, 2-Chloro-4-methylsulphonylbenzoic acid serves as an intermediate in the synthesis of drugs and active pharmaceutical ingredients (APIs). The compound's functional groups allow for further chemical modification, which is essential in the development of drug candidates with desired therapeutic properties. For example, the carboxylic acid group can be used to form esters or amides, which are common motifs in drug molecules. Additionally, the chloro and methylsulfonyl groups can be retained or replaced to fine-tune the pharmacokinetic and pharmacodynamic properties of the final drug molecule.

Moreover, 2-Chloro-4-methylsulphonylbenzoic acid finds application in materials science. The compound's ability to participate in polymerization reactions makes it a useful monomer in the synthesis of specialized polymers. These polymers can be designed to have specific mechanical, thermal, or chemical properties, making them suitable for use in coatings, adhesives, and other advanced materials. The electron-withdrawing nature of the methylsulfonyl group also contributes to the stability and durability of the resulting materials.

In summary, 2-Chloro-4-methylsulphonylbenzoic acid is a versatile chemical compound with significant applications in organic synthesis, agrochemicals, pharmaceuticals, and materials science. Its discovery as a derivative of benzoic acid has led to its use in the creation of more complex molecules and specialized materials, highlighting its importance in both scientific research and industrial applications.

References

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2024. Tandem catalysis enables chlorine-containing waste as chlorination reagents. Nature Chemistry, 16(5).
DOI: 10.1038/s41557-024-01462-8