Sodium 4-nitrobenzenemethanesulfonate
[CAS# 36639-50-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Sodium 4-nitrobenzenemethanesulfonate
• Synonyms: Sodium 4-nitrobenzylsulfonate; 4-Nitrobenzenemethanesulfonic acid sodium salt
• Molecular Formula: C₇H₆NO₅S^.Na
• Molecular Weight: 239.18
• CAS Registry Number: 36639-50-6
• EC Number: 609-277-8
• SMILES: C1=CC(=CC=C1CS(=O)(=O)[O-])[N+](=O)[O-].[Na+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Discovory and Applicatios

Sodium 4-nitrobenzenemethanesulfonate is an organic sodium salt composed of a 4-nitrobenzylsulfonate anion paired with a sodium cation. Structurally, the compound features a benzene ring substituted at the para position with a nitro group (-NO₂) and a methanesulfonate group (-CH₂SO₃^-). The sodium ion balances the negative charge on the sulfonate moiety, forming an ionic salt.

This compound belongs to the class of aromatic sulfonate salts, which are valued for their solubility in water and ability to serve as intermediates in organic synthesis. The nitro substituent on the benzene ring is an electron-withdrawing group that influences the electronic properties and reactivity of the molecule, while the sulfonate group provides hydrophilicity and ionic character.

Sodium 4-nitrobenzenemethanesulfonate is typically synthesized by sulfonation of 4-nitrobenzyl derivatives or by oxidation of corresponding sulfides, followed by neutralization with sodium hydroxide. The resulting compound is a crystalline solid that is readily soluble in aqueous media due to its ionic nature.

Applications of this compound are primarily in chemical synthesis, where it can act as a precursor for the introduction of sulfonate functionalities or as a leaving group in nucleophilic substitution reactions. Its water solubility and stability make it useful in reactions conducted in polar solvents or aqueous environments.

The nitro group offers a site for further chemical modification, such as reduction to an amine, enabling the preparation of aminobenzylsulfonate derivatives. These derivatives have potential uses in pharmaceuticals, dyes, and materials science.

Physicochemical properties include moderate polarity and high solubility in water. The compound is generally stable under standard laboratory conditions but may decompose under strong acidic or reducing environments.

Analytical characterization is achieved through techniques such as nuclear magnetic resonance (NMR) spectroscopy, which confirms the aromatic and methylene proton environments, infrared (IR) spectroscopy highlighting characteristic sulfonate and nitro group absorptions, and mass spectrometry for molecular weight confirmation.

In summary, sodium 4-nitrobenzenemethanesulfonate is a water-soluble aromatic sulfonate salt featuring a para-nitro substitution on the benzyl moiety. It serves as an important intermediate in organic synthesis with versatile functional groups enabling diverse chemical transformations.