6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide
[CAS# 4509-11-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfone, sulfoxide compound
• Name: 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide
• Synonyms: 3,4-Epoxytetrahydrothiophene-1,1-dioxide; 6-oxa-3?6-thiabicyclo[3.1.0]hexane 3,3-dioxide
• Molecular Formula: C₄H₆O₃S
• Molecular Weight: 134.15
• CAS Registry Number: 4509-11-9
• EC Number: 224-827-3
• SMILES: C1C2C(O2)CS1(=O)=O

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 145-150 ºC (Expl.)
• Index of Refraction: 1.547, Calc.^*
• Boiling Point: 379.2±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 183.1±25.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary 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
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide is an organic compound characterized by its bicyclic structure, which consists of both oxygen and sulfur heteroatoms integrated into a six-membered ring system. The compound is a member of the class of bicyclic compounds, specifically the bicyclo[3.1.0]hexane derivatives, which are known for their interesting chemical properties and reactivity. This particular structure contains a sulfur atom at the bridgehead position, connected to an oxygen atom, with the remainder of the ring exhibiting a degree of strain due to the fused heterocyclic rings. The presence of the 3,3-dioxide functionality further adds to the compound’s unique chemical characteristics.

The discovery of 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide dates back to the mid-20th century when chemists were exploring various bicyclic and heterocyclic systems for their reactivity and stability. These systems, due to their strained rings and incorporation of heteroatoms, can often serve as intermediates in organic reactions or as models for studying reactivity in strained organic compounds. Over time, this class of compounds, including 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide, has been of interest to synthetic chemists because of the ring strain, which can often lead to enhanced reactivity in chemical transformations.

In organic synthesis, 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide serves as a useful intermediate for the preparation of more complex molecules. The presence of both oxygen and sulfur atoms in the bicyclic structure makes it versatile for various chemical reactions, including nucleophilic substitution, cycloaddition, and rearrangement reactions. The strained nature of the bicyclic system allows it to undergo these transformations under relatively mild conditions, making it a valuable starting material in synthetic organic chemistry.

One notable application of 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide is in the synthesis of other heterocyclic compounds, particularly those used in pharmaceuticals and agrochemicals. The oxygen and sulfur atoms in the structure can participate in various functional group transformations, which may lead to the creation of biologically active molecules. For instance, derivatives of 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide have been explored in drug design, particularly in the context of developing molecules with antimicrobial or anticancer properties. The strained bicyclic ring also offers an opportunity for researchers to create compounds with high reactivity or binding affinity for specific biological targets.

In addition to pharmaceutical applications, the compound has also been investigated for its potential uses in material science. The strained ring systems of 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide may be useful in the synthesis of novel polymers or as building blocks for the creation of functional materials, including those with specific electrical, optical, or mechanical properties. The compound's ability to participate in chemical reactions that form larger structures makes it an attractive candidate for the development of advanced materials with unique properties.

Moreover, the heteroatom incorporation within the bicyclic structure lends 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide a potential role in catalysis. The oxygen and sulfur atoms may act as Lewis bases or coordinate to transition metals, enhancing catalytic activity in organic reactions. This feature opens up possibilities for its use in catalytic cycles, particularly in reactions that involve electron-rich centers or where the formation of strained intermediates is beneficial.

In conclusion, 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide is an intriguing compound with a unique bicyclic structure that makes it valuable in organic synthesis, pharmaceutical development, and material science. Its reactivity and the ability to participate in a range of chemical transformations give it versatility as an intermediate in the creation of biologically active compounds and functional materials. As research continues into the synthesis and applications of bicyclic heterocyclic compounds, 6-Oxa-3-thiabicyclo[3.1.0]hexane 3,3-dioxide is likely to remain a subject of interest for chemists seeking to explore its potential.

References

A. Mateo Alonso, Roberto Horcajada, Majid Motevalli, James H. P. Utley and Peter B. Wyatt. The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation, Org. Biomol. Chem., 2005, 3, 2842.