Disodium 3,3'-sulfonylbis(6-chlorobenzenesulfonate)
[CAS# 51698-33-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfone, sulfoxide compound
• Name: Disodium 3,3'-sulfonylbis(6-chlorobenzenesulfonate)
• Synonyms: 4,4'-Dichlorodiphenylsulfone-3,3'-disulfonic acid disodium salt
• Molecular Formula: C₁₂H₆Cl₂Na₂O₈S₃
• Molecular Weight: 491.25
• CAS Registry Number: 51698-33-0
• EC Number: 685-971-4
• SMILES: C1=CC(=C(C=C1S(=O)(=O)C2=CC(=C(C=C2)Cl)S(=O)(=O)[O-])S(=O)(=O)[O-])Cl.[Na+].[Na+]

Properties

• Melting point: >300 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H318
• Precautionary Statements: P264+P265-P280-P305+P354+P338-P317

Hazard Classification

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

Discovory and Applicatios

Disodium 3,3’-sulfonylbis(6-chlorobenzenesulfonate) is an organic sulfonate compound characterized by two 6-chlorobenzenesulfonate units connected through a sulfonyl (SO₂) bridge at the 3 and 3’ positions of the aromatic rings. The compound exists as a disodium salt, indicating the presence of two sodium ions that balance the negative charges on the sulfonate groups. The chlorine substituents on the benzene rings influence the compound’s electronic properties and chemical reactivity.

Structurally, the molecule comprises two chlorobenzenesulfonate moieties linked via a sulfonyl functional group, forming a bis-sulfonate derivative. The sulfonate groups (–SO₃^–) are strong acidic groups, usually present in their salt form to enhance solubility in aqueous media and to improve handling properties.

Synthesis of disodium 3,3’-sulfonylbis(6-chlorobenzenesulfonate) typically involves sulfonation of appropriately substituted chlorobenzenes, followed by oxidative coupling to introduce the sulfonyl bridge. The resulting bis-sulfonate compound is then neutralized with sodium hydroxide or sodium carbonate to form the disodium salt. Precise control of reaction conditions is necessary to ensure regioselectivity and high purity.

Chemically, the compound exhibits properties typical of sulfonate salts, such as high solubility in water and stability under acidic and basic conditions. The presence of chlorine atoms imparts electron-withdrawing effects, which can influence the acidity of the sulfonate groups and the compound’s reactivity toward nucleophiles and electrophiles. The sulfonyl linkage provides rigidity and affects molecular conformation.

Applications of disodium 3,3’-sulfonylbis(6-chlorobenzenesulfonate) are mainly in industrial chemistry and materials science. It can serve as an intermediate in the synthesis of dyes, surfactants, and polymer additives. Its water solubility and chemical stability make it useful in formulations requiring ionic surfactants or ionic crosslinkers. Additionally, the compound’s unique structure may be employed in specialized chemical processes where bifunctional sulfonate groups are beneficial.

Analytical characterization includes nuclear magnetic resonance (¹H and ¹³C NMR) spectroscopy to confirm the aromatic framework and substitution pattern. Infrared (IR) spectroscopy identifies characteristic sulfonate (S=O) stretches near 1200 and 1050 cm^–1, as well as C–Cl bond vibrations. Mass spectrometry provides molecular weight confirmation and fragmentation consistent with the bis-sulfonate structure. Elemental analysis verifies sodium and chlorine content.

Physically, disodium 3,3’-sulfonylbis(6-chlorobenzenesulfonate) is generally obtained as a water-soluble crystalline solid or powder. Its aqueous solutions exhibit ionic conductivity, and the compound is stable under normal storage conditions. Handling precautions typically focus on avoiding exposure to moisture and controlling dust.

In summary, disodium 3,3’-sulfonylbis(6-chlorobenzenesulfonate) is a bifunctional sulfonate salt featuring chlorinated aromatic rings linked by a sulfonyl bridge. Its chemical and physical properties make it valuable as an intermediate and functional additive in various chemical industries, with well-established methods of synthesis and characterization.