Sodium 4-chloro-3-formylbenzene-1-sulfonate
[CAS# 42481-01-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Sodium 4-chloro-3-formylbenzene-1-sulfonate
• Synonyms: 2-Chlorobenzaldehyde-5-sulfonic acid sodium salt
• Molecular Formula: C₇H₄ClNaO₄S
• Molecular Weight: 242.61
• CAS Registry Number: 42481-01-6
• SMILES: C1(=CC=C(C(=C1)C=O)Cl)[S](=O)(=O)[O-].[Na+]

Discovery and Applications

Sodium 4-chloro-3-formylbenzene-1-sulfonate is an important aromatic compound widely used as an intermediate in organic synthesis. This molecule features a benzene ring with a chlorine atom, a formyl group, and a sulfonate group. The sodium salt enhances its solubility in water and provides greater stability for handling in various chemical processes. The combination of these functional groups allows it to participate in multiple types of chemical reactions, making it valuable in pharmaceutical, agrochemical, and material industries.

The discovery of sodium 4-chloro-3-formylbenzene-1-sulfonate can be traced back to early research on aromatic sulfonation and formylation reactions. These reactions were developed to introduce functional groups onto aromatic rings in a controlled manner. Researchers found that the chlorination of aromatic compounds followed by sulfonation and subsequent formylation produced derivatives with versatile reactivity. The sodium salt form was selected to enhance the compound's solubility and facilitate its use in aqueous-based reactions.

The synthesis of sodium 4-chloro-3-formylbenzene-1-sulfonate typically involves a multi-step process. Initially, 4-chlorobenzene-1-sulfonic acid is prepared by the sulfonation of chlorobenzene. This intermediate undergoes a formylation reaction, often using reagents such as hexamethylenetetramine (HMTA) under acidic conditions or the Gattermann-Koch reaction to introduce the formyl group at the meta position relative to the sulfonate. Finally, the sulfonic acid group is neutralized with sodium hydroxide to form the sodium salt. This method is favored for its efficiency and reproducibility in industrial applications.

This compound finds application in the synthesis of pharmaceuticals and agrochemicals. The formyl group serves as a versatile handle for further chemical modifications, such as the formation of imines, oximes, and heterocyclic compounds. The sulfonate group enhances the water solubility of intermediates, which is particularly useful in developing drugs with better bioavailability. Additionally, derivatives of this compound are used in the synthesis of dyes and pigments, where the sulfonate group improves dye solubility and fixation properties.

Ongoing research aims to optimize the synthesis of sodium 4-chloro-3-formylbenzene-1-sulfonate and explore its potential in new chemical applications. Its unique combination of functional groups continues to make it a valuable building block in synthetic chemistry and industrial processes.

References

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