1,2-Oxathiolan-5-one, 2,2-dioxide
[CAS# 5961-88-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 1,2-Oxathiolan-5-one, 2,2-dioxide
• Synonyms: 2,2-dioxooxathiolan-5-one; B-SulfopropionicAnhydride
• Molecular Formula: C₃H₄O₄S
• Molecular Weight: 136.13
• CAS Registry Number: 5961-88-6
• EC Number: 833-074-5
• SMILES: C1CS(=O)(=O)OC1=O

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.505, Calc.^*
• Boiling Point: 247.9±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 103.8±22.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,2-Oxathiolan-5-one, 2,2-dioxide is an organic sulfur compound that has attracted attention due to its unique chemical structure and potential applications in various fields, particularly in synthetic chemistry and pharmaceutical development. This compound is part of a broader class of heterocyclic compounds known for incorporating both sulfur and oxygen atoms within a ring structure. The name 1,2-Oxathiolan-5-one, 2,2-dioxide describes the specific arrangement of atoms in the molecule, which includes a sulfur atom adjacent to an oxygen atom in a five-membered ring structure, along with a carbonyl group (C=O) at the 5-position.

The discovery of 1,2-Oxathiolan-5-one, 2,2-dioxide emerged from research on sulfur-containing heterocycles and their ability to participate in a variety of chemical reactions. The compound's structure, which consists of a sulfur-oxygen ring, provides interesting reactivity due to the electron-rich nature of sulfur and oxygen, allowing for interactions with other chemical species. This reactivity has made it a subject of research in fields such as catalysis and the synthesis of more complex molecules.

In terms of applications, 1,2-Oxathiolan-5-one, 2,2-dioxide has found use in several areas of organic synthesis. It has been utilized as a key intermediate in the formation of other sulfur-containing compounds, which are valuable in the development of agrochemicals, pharmaceuticals, and functional materials. Its ability to undergo various chemical transformations makes it a useful building block for creating molecules with diverse functional groups, which can be employed in the development of drugs and other specialty chemicals.

One of the most promising applications of 1,2-Oxathiolan-5-one, 2,2-dioxide lies in the field of pharmaceutical chemistry. The compound has been investigated for its potential to interact with biological systems, particularly in the design of new drug candidates. Its sulfur-oxygen structure is thought to contribute to its ability to interact with enzymes and receptors, making it a candidate for further study in drug discovery and design. Researchers have explored its potential in the development of drugs that target specific biological pathways, such as those involved in inflammation and cancer.

Furthermore, the compound's ability to form stable derivatives has led to its exploration in material science. 1,2-Oxathiolan-5-one, 2,2-dioxide and its derivatives have been examined for their properties in conducting polymers, which have applications in electronics and energy storage devices. The stability and reactivity of the compound make it a valuable tool for developing new materials with tailored properties, such as sensors or light-emitting devices.

As research into the properties and applications of 1,2-Oxathiolan-5-one, 2,2-dioxide continues, it is likely that new uses will emerge, particularly in the fields of material science, pharmaceuticals, and green chemistry. Its unique structure, combined with its ability to participate in a variety of chemical reactions, ensures that it will remain an important compound for synthetic chemists and researchers alike.

References

2007. Stereospecific Synthesis of Optically Active (Acylamino)(acyloxy)diarylspiro-λ4-sulfanes. *Science of Synthesis*. URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-020-01434

2004. From Alkoxy- or Aminosulfonium Salts. *Science of Synthesis*. URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-027-00066