4-Methyl-1,2-oxathiolane 2,2-dioxide
[CAS# 15606-89-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate
• Name: 4-Methyl-1,2-oxathiolane 2,2-dioxide
• Synonyms: 4-methyloxathiolane 2,2-dioxide
• Molecular Formula: C₄H₈O₃S
• Molecular Weight: 136.17
• CAS Registry Number: 15606-89-0
• SMILES: CC1COS(=O)(=O)C1

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.459, Calc.^*
• Boiling Point: 280.8±9.0 ºC (760 mmHg), Calc.^*
• Flash Point: 123.6±18.7 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+351+338-P302+352

Discovory and Applicatios

4-Methyl-1,2-oxathiolane 2,2-dioxide, commonly recognized as a cyclic sulfonate ester, is an organosulfur compound that has gained attention for its unique chemical properties and synthetic utility. Structurally, it features a five-membered ring containing sulfur, oxygen, and a methyl group attached to the carbon adjacent to the sulfur. The sulfonate group provides electrophilic character, while the ring structure confers rigidity and specificity to its reactions.

The initial discovery of 4-methyl-1,2-oxathiolane 2,2-dioxide stemmed from studies into sulfonate esters as intermediates for stereospecific transformations. Researchers exploring cyclic sulfonates found that incorporating methyl groups into the ring significantly enhanced the stability and reactivity of these compounds. The methyl group not only influences steric effects but also modulates the electronic environment of the ring, making this compound useful in selective substitution reactions.

The synthesis of 4-methyl-1,2-oxathiolane 2,2-dioxide typically involves the cyclization of appropriate 2-hydroxyalkanesulfonic acids or their derivatives. One well-established method uses 4-methyl-1,2-ethanediol and sulfuryl chloride under controlled conditions. This process results in ring closure to form the stable cyclic sulfonate. The reaction proceeds efficiently and yields a product that is readily purified and stored, making it an attractive candidate for synthetic applications.

This compound has found numerous applications in organic synthesis. One prominent use is as a leaving group in nucleophilic substitution reactions. The sulfonate moiety is an excellent leaving group due to the stability of the resulting sulfonic acid derivative. This property makes 4-methyl-1,2-oxathiolane 2,2-dioxide an effective reagent for introducing functional groups, such as amines or alkoxides, into complex molecules. The rigidity of the ring system can also influence reaction pathways, enabling selective transformations that are difficult to achieve with linear sulfonates.

In pharmaceutical chemistry, cyclic sulfonates like 4-methyl-1,2-oxathiolane 2,2-dioxide are used as intermediates in the synthesis of antiviral agents and other bioactive molecules. The controlled reactivity and stability of this compound make it valuable in multi-step syntheses where maintaining stereochemical integrity is critical. Researchers have also explored its role in synthesizing chiral molecules, leveraging its structure to achieve stereospecific outcomes.

Additionally, this compound is of interest in polymer chemistry. It can be incorporated as a monomer or crosslinking agent in the production of specialty polymers. The sulfonate group can participate in controlled polymerization reactions, contributing to the development of materials with specific thermal and mechanical properties. These polymers are useful in applications ranging from medical devices to advanced coatings.

Overall, 4-methyl-1,2-oxathiolane 2,2-dioxide serves as a versatile reagent in organic synthesis, pharmaceutical development, and polymer chemistry, owing to its unique combination of structural stability and reactivity.