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1,1'-Thiobis(2,3-epithiopropane)
[CAS# 188829-97-2]

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Identification
Classification Organic raw materials >> Organic sulfur compound
Name 1,1'-Thiobis(2,3-epithiopropane)
Synonyms 2-(thiiran-2-ylmethylsulfanylmethyl)thiirane
Molecular Structure CAS # 188829-97-2, 1,1'-Thiobis(2,3-epithiopropane), 2-(thiiran-2-ylmethylsulfanylmethyl)thiirane
Molecular Formula C6H10S3
Molecular Weight 178.34
CAS Registry Number 188829-97-2
EC Number 831-368-8
SMILES C1C(S1)CSCC2CS2
Properties
Density 1.3±0.1 g/cm3, Calc.*
Index of Refraction 1.677, Calc.*
Boiling Point 317.5±7.0 ºC (760 mmHg), Calc.*
Flash Point 159.7±15.2 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol symbol   GHS07;GHS08 Warning    Details
Hazard Statements H302-H315-H373    Details
Precautionary Statements P260-P264-P270-P280-P301+P317-P302+P352-P319-P321-P330-P332+P317-P362+P364-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - repeated exposureSTOT RE2H373
up Discovory and Applicatios
1,1'-Thiobis(2,3-epithiopropane) is a chemical compound with a structure that includes two epithiopropane groups linked by a sulfur atom. This compound, commonly referred to as a bis-epoxide, is notable for its reactivity and is employed in a range of industrial applications, particularly in polymer chemistry and materials science. The discovery and utilization of 1,1'-Thiobis(2,3-epithiopropane) can be traced back to the broader development of epoxide chemistry, which gained momentum in the mid-20th century with the recognition of epoxides' utility as versatile intermediates in organic synthesis and materials production.

The unique structure of 1,1'-Thiobis(2,3-epithiopropane) includes two reactive epoxide rings, which can undergo various chemical reactions, particularly with nucleophiles. This reactivity makes the compound a valuable cross-linking agent, particularly in the production of thermosetting polymers. When used as a cross-linker, 1,1'-Thiobis(2,3-epithiopropane) reacts with functional groups in polymer chains, forming strong covalent bonds that enhance the mechanical properties, chemical resistance, and thermal stability of the resulting materials.

In polymer chemistry, 1,1'-Thiobis(2,3-epithiopropane) is used in the synthesis of epoxy resins, which are widely applied in coatings, adhesives, and composites. The compound’s ability to introduce cross-links into polymer networks results in materials with superior durability and resistance to environmental degradation. For instance, epoxy resins cured with 1,1'-Thiobis(2,3-epithiopropane) exhibit enhanced resistance to heat, moisture, and chemicals, making them ideal for protective coatings in automotive, aerospace, and marine applications.

Another significant application of 1,1'-Thiobis(2,3-epithiopropane) is in the field of rubber vulcanization. In this context, the compound acts as a vulcanizing agent, facilitating the formation of cross-linked networks within rubber materials. The cross-linking process improves the elasticity, strength, and durability of rubber products, which is essential for applications such as tires, seals, and gaskets. The use of 1,1'-Thiobis(2,3-epithiopropane) in vulcanization is particularly beneficial in producing high-performance rubber materials that must withstand harsh operational conditions.

In addition to its use in polymers and rubbers, 1,1'-Thiobis(2,3-epithiopropane) has been investigated for its potential in advanced material applications, including the development of high-performance coatings and adhesives. Its reactive epoxide groups can be tailored to interact with various substrates, making it a versatile additive for enhancing the adhesion properties of coatings and adhesives. This has led to its use in the formulation of products that require strong bonding to a variety of surfaces, including metals, plastics, and composites.

Moreover, the compound has been explored in the creation of specialty polymers with unique properties, such as enhanced flame retardance and resistance to degradation by ultraviolet (UV) light. These specialty polymers find use in critical applications where material failure is not an option, such as in electronics, aerospace components, and protective clothing.

The discovery and application of 1,1'-Thiobis(2,3-epithiopropane) illustrate the ongoing innovation in chemical synthesis and materials science. Its ability to enhance the properties of polymers, rubbers, and coatings has made it an indispensable component in numerous industrial processes. As research into advanced materials continues to evolve, compounds like 1,1'-Thiobis(2,3-epithiopropane) will likely play an increasingly important role in the development of new materials with improved performance characteristics.
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