Sodium 3-[[(dimethylamino)thioxomethyl]thio]propanesulphonate
[CAS# 18880-36-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Sodium 3-[[(dimethylamino)thioxomethyl]thio]propanesulphonate
• Synonyms: N,N-Dimethyl-dithiocarbamyl propyl sulfonic acid sodium salt; DPS
• Molecular Formula: C₆H₁₂NNaO₃S₃
• Molecular Weight: 265.35
• CAS Registry Number: 18880-36-9
• EC Number: 242-644-7
• SMILES: CN(C)C(=S)SCCCS(=O)(=O)[O-].[Na+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Discovery and Applications

Sodium 3-[[(dimethylamino)thioxomethyl]thio]propanesulphonate is a chemical compound with a unique structure that includes a dimethylamino group, a thioxomethyl group, and a propanesulfonate backbone. The discovery of this compound was primarily driven by the need for sulfur-containing intermediates in organic synthesis, especially in the development of pharmaceutical agents and specialty chemicals. Its multifunctional nature allows it to participate in a variety of chemical reactions, particularly those involving sulfur transfer, making it valuable in the synthesis of biologically active molecules.

One of the key features of this compound is its ability to serve as a thiolating agent due to the presence of the thioxomethyl group. Thiolation, or the introduction of sulfur into a molecular structure, is an important step in synthesizing a range of sulfur-containing compounds, including pharmaceuticals, agrochemicals, and functional materials. Sodium 3-[[(dimethylamino)thioxomethyl]thio]propanesulphonate can be used in the formation of thioethers and other sulfur-based functional groups, which are essential for imparting stability and biological activity to molecules.

In pharmaceutical research, this compound has found application in the modification of drug candidates. The incorporation of sulfur atoms into drug molecules can enhance their pharmacokinetic properties, such as improving solubility, bioavailability, and metabolic stability. Sodium 3-[[(dimethylamino)thioxomethyl]thio]propanesulphonate serves as a versatile reagent in this context, allowing for the efficient synthesis of sulfur-containing drugs and intermediates.

Moreover, the propanesulfonate moiety of the compound provides water solubility, which is a significant advantage in aqueous-phase reactions. This makes it suitable for use in bioconjugation and other processes that require water-soluble reagents. The dimethylamino group also enhances the nucleophilicity of the molecule, enabling it to participate in a wide range of organic transformations, such as nucleophilic substitution and addition reactions.

This compound is also explored in the development of functional materials, particularly in the field of polymers and coatings, where sulfur-containing crosslinkers and stabilizers are needed to improve material properties. The ability of sodium 3-[[(dimethylamino)thioxomethyl]thio]propanesulphonate to introduce sulfur atoms into polymer networks has been utilized to enhance the thermal and mechanical properties of polymer-based materials, making them more resistant to environmental degradation and mechanical stress.

References

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