(4R)-4-Methyl-1,3,2-dioxathiolane 2,2-dioxide
[CAS# 1006381-03-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (4R)-4-Methyl-1,3,2-dioxathiolane 2,2-dioxide
• Synonyms: (R)-4-Methyl-1,3,2-dioxathiolane 2,2-dioxide
• Molecular Formula: C₃H₆O₄S
• Molecular Weight: 138.14
• CAS Registry Number: 1006381-03-8
• EC Number: 830-083-6
• SMILES: C[C@@H]1COS(=O)(=O)O1

Properties

• Solubility: Soluble (87 g/L) (25 ºC), Calc.^*
• Density: 1.418±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.450, Calc.^*
• Boiling point: 221.8±7.0 ºC (760 Torr), Calc.^*
• Flash point: 88.0±18.2 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H302-H341
• Precautionary Statements: P203-P264-P270-P280-P301+P317-P318-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

(4R)-4-Methyl-1,3,2-dioxathiolane 2,2-dioxide is an organosulfur compound known for its distinct cyclic structure and stereospecific methyl substitution. This compound, commonly referred to as methylated cyclic sulfite, exhibits properties that make it useful in chemical synthesis and as an intermediate in various industrial processes.

The compound’s discovery stems from early studies on sulfur-containing heterocycles. These investigations sought to explore the reactivity and stability of dioxathiolane derivatives under diverse conditions. The synthesis of (4R)-4-methyl-1,3,2-dioxathiolane 2,2-dioxide typically involves the reaction of sulfurous acid derivatives with methyl-substituted epoxides. This pathway provides high yields and allows control over the stereochemistry, enabling the isolation of the (4R) enantiomer with high purity.

A key application of this compound lies in its role as a chiral auxiliary in asymmetric synthesis. The stereospecific configuration of the methyl group at the 4-position allows for the induction of chirality in subsequent reactions, making it a valuable tool in the preparation of enantiomerically pure pharmaceuticals and agrochemicals. Its cyclic sulfite structure also facilitates selective interactions with nucleophiles, broadening its utility in organic transformations.

In material sciences, (4R)-4-methyl-1,3,2-dioxathiolane 2,2-dioxide serves as a precursor in the synthesis of sulfur-containing polymers. These polymers exhibit unique thermal and mechanical properties, making them suitable for advanced applications, including high-performance coatings and membranes. The compound's stability and controlled reactivity are key attributes that contribute to its effectiveness in polymer chemistry.

The compound is also explored for its potential in energy storage systems, particularly as an additive in electrolyte formulations for lithium-ion batteries. Its sulfur content and cyclic structure help enhance the ionic conductivity and thermal stability of electrolyte solutions, contributing to improved battery performance and safety.

While (4R)-4-methyl-1,3,2-dioxathiolane 2,2-dioxide offers considerable benefits in various applications, its handling requires careful attention due to its potential as an irritant. Proper storage and adherence to safety protocols are necessary to minimize risks associated with its use.

Ongoing research continues to investigate the full range of this compound’s capabilities, including novel applications in green chemistry and sustainable materials. Its combination of functional diversity and stereochemical specificity ensures its continued significance in scientific and industrial advancements.