1,2-Bis(2-mercaptoethoxy)ethane
[CAS# 14970-87-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol salt
• Name: 1,2-Bis(2-mercaptoethoxy)ethane
• Synonyms: 3,6-Dioxa-1,8-octanedithiol
• Molecular Formula: C₆H₁₄O₂S₂
• Molecular Weight: 182.3
• CAS Registry Number: 14970-87-7
• EC Number: 239-044-2
• SMILES: C(COCCS)OCCS

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.495, Calc.^*, 1.509 (Expl.)
• Boiling Point: 257.0±30.0 ºC (760 mmHg), Calc.^*, 225 ºC (Expl.)
• Flash Point: 109.2±24.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS09 Danger
• Hazard Statements: H301-H302+H332-H302-H332-H400-H410-H411
• Precautionary Statements: P261-P264-P270-P271-P273-P301+P316-P301+P317-P304+P340-P317-P321-P330-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	3	H301
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

1,2-Bis(2-mercaptoethoxy)ethane, also known as bis(2-mercaptoethyl) ether, is a sulfur-containing organic compound that plays a significant role in various chemical and industrial applications. This compound consists of an ethane backbone with two mercaptoethoxy groups attached to the carbon atoms at positions 1 and 2. The mercapto groups (–SH) contribute to the compound's unique chemical reactivity and make it useful in a variety of applications, particularly in fields requiring high reactivity and specific bonding characteristics.

The discovery of 1,2-bis(2-mercaptoethoxy)ethane can be attributed to the ongoing research into thiol-based compounds, which have been of interest due to their diverse chemical properties. Thiol groups, due to their sulfur atom, exhibit a wide range of reactivity, particularly in forming bonds with metals, which gives rise to the compound's significant utility in applications involving metal chelation, polymer synthesis, and more. Researchers have studied mercapto-based compounds extensively for their ability to act as chelating agents, antioxidants, and stabilizers in chemical processes.

In terms of its structure, 1,2-bis(2-mercaptoethoxy)ethane is classified as a bis-mercaptoethanol derivative, where each mercaptoethoxy group consists of an ethoxy (-OCH2CH2-) linker and a thiol group (-SH). This configuration makes it highly reactive, allowing it to participate in numerous chemical reactions, including nucleophilic substitutions, coordination with metal ions, and the formation of disulfide linkages under specific conditions. The compound's ability to form stable complexes with various metals is one of the key reasons it is widely employed in both research and industry.

The most notable application of 1,2-bis(2-mercaptoethoxy)ethane is in the field of coordination chemistry, where it is used as a chelating agent for metal ions. It forms stable complexes with transition metals such as copper, nickel, and zinc, which are crucial in the development of catalysts for industrial chemical reactions. These metal complexes are often used in the production of polymers, in environmental cleanup processes, and in the synthesis of various organic compounds. By coordinating with metal ions, 1,2-bis(2-mercaptoethoxy)ethane enhances the stability of these metal catalysts, thus improving their efficiency and lifespan.

In addition to its role as a chelating agent, 1,2-bis(2-mercaptoethoxy)ethane is also used as a stabilizer and antioxidant in polymer science. The mercapto groups are capable of scavenging free radicals, which helps prevent the degradation of sensitive materials during processing and in end-use applications. This property is particularly beneficial in industries such as plastics, rubber, and coatings, where maintaining the stability of materials over time is crucial. It is used in stabilizing polyolefins, for example, by reducing oxidative degradation, thereby enhancing the longevity and performance of the final product.

Another significant application of 1,2-bis(2-mercaptoethoxy)ethane is in biomedical research, where it is explored for its potential in drug delivery systems and as a component in therapeutic agents. The compound's ability to form stable complexes with metals and its reactivity with certain biomolecules have led researchers to investigate its use in targeted drug delivery, particularly for diseases that require localized treatments. Additionally, its antioxidant properties make it an interesting candidate for use in pharmaceutical formulations designed to combat oxidative stress in the body.

1,2-bis(2-mercaptoethoxy)ethane is also utilized in various surface modification applications. Its thiol groups are known for their ability to bind to metal surfaces, such as gold and silver, forming stable self-assembled monolayers. This property is exploited in the production of sensors, where the compound is used to modify the surfaces of electrodes to enhance the detection of specific chemical or biological targets. These sensors are widely used in environmental monitoring, medical diagnostics, and food safety testing.

In conclusion, 1,2-bis(2-mercaptoethoxy)ethane is a versatile compound with a wide range of applications in both research and industrial fields. Its unique chemical properties, particularly its ability to chelate metal ions and scavenge free radicals, make it an important component in coordination chemistry, polymer stabilization, biomedical research, and surface modification technologies. As a result, it continues to play a key role in advancing various technologies that require the reactivity and stability provided by thiol-containing compounds.